Alkene-containing carboxylate compound and use thereof

ABSTRACT

An alkene-containing carboxylic ester compound of formula (I) and its agriculturally acceptable salt can be used as a herbicide.

TECHNICAL FIELD

The present invention belongs to the field of herbicides, and particularly relates to an alkene-containing carboxylic ester compound and an application thereof.

BACKGROUND

Due to the succession and change of weed populations and the emergence and rapid development of resistance to chemical pesticides, people have continuously strengthened awareness on ecological environmental protection, and have paid more attention to the knowledge of chemical pesticide pollution and the influence of pesticides on non-target organisms and the end-result problem in the pesticide ecological environment. With the gradual decrease of the arable land area in the world, the continuous increase of the population and the increase of the demands for food, people are forced to rapidly develop agricultural production technologies, enhance and improve the farming system, and continuously invent novel and improved herbicidal compounds and compositions.

DE 2513750A1 has reported that some benzoyl pyrazole compounds have herbicidal activity, such as compound 79 (KC₁):

WO 0003993A1 has reported that some benzoyl pyrazole compounds have herbicidal activity, such as compound 357 (KC₂):

The alkene-containing carboxylic ester compound shown in the present invention is not disclosed.

SUMMARY

The purpose of the present invention is to provide an alkene-containing carboxylic ester compound with novel structure and safety for crops and an application thereof as a herbicide.

To achieve the above purpose, the present invention adopts the following technical solution: An alkene-containing carboxylic ester compound is shown in formula I:

in the formula:

X₁ is selected from hydrogen, cyano, nitro, halogen, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkoxy C₁-C₃ alkyl, C₁-C₆ alkoxy C₁-C₃ alkoxy, C₁-C₆ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₃ alkyl, C₃-C₆ cycloalkyl C₁-C₃ alkoxy, C₃-C₆ cycloalkyloxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl, C₂-C₆ alkenylsulfonyl, C₂-C₆ alkynylsulfonyl, phenylsulfonyl, C₂-C₆ alkenyloxy, C₂-C₆ alkynyloxy, phenyloxy, C₂-C₆ alkenylthio, C₂-C₆ alkynylthio, phenylthio, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₃-C₆ cycloalkyl;

W is selected from N or CX₂;

X₂ is selected from hydrogen, cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₃-C₆ halocycloalkyl C₁-C₆ alkyl, Y₁ oxy, Y₁ thio, Y₁Y₂ amino, Y₁ sulfinyl, Y₁ sulfonyl, Y₁ oxy C₁-C₆ alkyl, Y₁ thio C₁-C₆ alkyl, YjY2 amino C₁-C₆ alkyl, Y₁ sulfinyl C₁-C₆ alkyl, Y₁ sulfonyl C₁-C₆ alkyl, C(O)Y₁, C(O)OY₁, OC(O)OY₁, N(Y₁)C(O)OY₂, C(O)N(Y₁)Y₂, N(Y₁)C(O)N(Y₁)Y₂, OC(O)N(Y₁)Y₂, C(O)N(Y₁)OY₂, N(Y₁)S(O)₂Y₂, N(Y₁)C(O)Y₂, OS(O)₂Y₁, CH═NOY₁, C₁-C₆ alkyl-CH═NOY₁, C₁-C₆ alkyl-O—N═C(Y₁)Y₂, phenyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkoxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl or halophenyl;

Y₁ and Y₂ are independently selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkoxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl or halophenyl;

X₃ is selected from hydrogen, cyano, nitro, halogen, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkoxy C₁-C₃ alkyl, C₁-C₆ alkoxy C₁-C₃ alkoxy, C₁-C₆ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₃ alkyl, C₃-C₆ cycloalkyl C₁-C₃ alkoxy, C₃-C₆ cycloalkyloxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₆ alkenylsulfonyl, C₂-C₆ alkynylsulfonyl, C₂-C₆ alkenyloxy, C₂-C₆ alkynyloxy, C₂-C₆ alkenylthio, C₂-C₆ alkynylthio, phenyl, phenyloxy, phenylthio, phenylsulfonyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered alicyclic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; hydrogen on the phenyl, aliphatic heterocycle and aromatic heterocycle mentioned above may be substituted with one or more of the following substituents selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₃-C₆ cycloalkyl;

-   -   when X₁ is selected from chlorine and X₃ is selected from         methylsulfonyl, X₂ is not 2-thiazolyl;

Z₁ is selected from C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkylsulfonyl C₁-C₆ alkyl or phenyl;

Z₂ is selected from H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or C₁-C₆ haloalkyl;

Q is selected from Q₁ or Q₂ group;

Q₂ is selected from C₃-C₈ cycloalkenyl; the hydrogen on the ring can be substituted by the following substituents; the following substituents are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkenyl or C₃-C₆ cycloalkyl;

when Q is selected from Q₂, Z₂ is not cyclopropyl;

R₁ to R₅ are independently selected from hydrogen, cyano, nitro, halogen, phenyl, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio or benzyloxy;

wherein R₁ and R₂ form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring;

R₂ and R₃ can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring;

a stereoisomer of the compound of the above formula I; or, the compound of the formula I and agriculturally acceptable salt of the isomer.

A preferred compound is: in the formula I:

X₁ is selected from hydrogen, cyano, nitro, halogen, C₁-C₆ alkylsulfonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkoxy C₁-C₃ alkyl, C₁-C₆ alkoxy C₁-C₃ alkoxy, C₁-C₆ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₁-C₃ alkoxy, C₃-C₆ cycloalkyloxy, C₂-C₆ alkenyloxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl, phenylsulfonyl, phenyloxy, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms and a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₃-C₆ cycloalkyl;

W is selected from N or CX₂;

X₂ is selected from hydrogen, cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₃-C₆ halocycloalkyl C₁-C₆ alkyl, Y₁ oxy, Y₁ thio, Y₁Y₂ amino, Y₁ sulfinyl, Y₁ sulfonyl, Y₁ oxy C₁-C₆ alkyl, Y₁ thio C₁-C₆ alkyl, Y₁Y₂ amino C₁-C₆ alkyl, Y₁ sulfinyl C₁-C₆ alkyl, Y₁ sulfonyl C₁-C₆ alkyl, C(O)Y₁, C(O)OY₁, OC(O)OY₁, N(Y₁)C(O)OY₂, C(O)N(Y₁)Y₂, N(Y₁)C(O)N(Y₁)Y₂, OC(O)N(Y₁)Y₂, C(O)N(Y₁)OY₂, N(Y₁)S(O)₂Y₂, N(Y₁)C(O)Y₂, OS(O)₂Y₁, CH═NOY₁, C₁-C₆ alkyl-CH═NOY₁, C₁-C₆ alkyl-O—N═C(Y₁)Y₂, phenyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy;

Y₁ and Y₂ are independently selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy;

X₃ is selected from hydrogen, cyano, halogen, C₁-C₆ alkylsulfonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkoxy C₁-C₃ alkyl, C₁-C₆ alkoxy C₁-C₃ alkoxy, C₁-C₆ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₁-C₃ alkoxy, C₃-C₆ cycloalkyloxy, C₂-C₆ alkenyloxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl, phenylsulfonyl, phenyloxy, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms and a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₃-C₆ cycloalkyl;

when X₁ is selected from chlorine and X₃ is selected from methylsulfonyl, X₂ is not 2-thiazolyl;

Z₁ is selected from C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl or phenyl;

Z₂ is selected from H, C₁-C₆ alkyl, C₁-C₆ haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or C₁-C₆ haloalkyl;

Q is selected from Q₁ or Q₂ group;

Q₂ is selected from C₃-C₈ cycloalkenyl; the hydrogen on the ring can be substituted by the following substituents; the following substituents are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkenyl or C₃-C₆ cycloalkyl; R₁ to R₅ are independently selected from hydrogen, cyano, nitro, halogen, phenyl, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio or benzyloxy;

wherein R₁ and R₂ form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring;

R₂ and R₃ can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring;

the Q of the above formula I is selected from a stereoisomer of the compound shown by Q₁.

A further preferred compound is: in the formula I:

X₁ is selected from hydrogen, cyano, nitro, halogen, C₁-C₃ alkylsulfonyl, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ alkoxy C₁-C₃ alkyl, C₁-C₃ alkoxy C₁-C₃ alkoxy, C₁-C₃ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkyloxy;

W is selected from N or CX₂;

X₂ is selected from hydrogen, cyano, nitro, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₃ alkyl, C₃-C₆ halocycloalkyl C₁-C₃ alkyl, Y₁ oxy, Y₁ thio, Y₁Y₂ amino, Y₁ sulfinyl, Y₁ sulfonyl, Y₁ oxy C₁-C₃ alkyl, Y₁ thio C₁-C₃ alkyl, Y₁Y₂ amino C₁-C₃ alkyl, Y₁ sulfinyl C₁-C₃ alkyl, Y₁ sulfonyl C₁-C₃ alkyl, C(O)Y₁, C(O)OY₁, OC(O)OY₁, N(Y₁)C(O)OY₂, C(O)N(Y₁)Y₂, N(Y₁)C(O)N(Y₁)Y₂, OC(O)N(Y₁)Y₂, C(O)N(Y₁)OY₂, N(Y₁)S(O)₂Y₂, N(Y₁)C(O)Y₂, OS(O)₂Y₁, CH═NOY₁, C₁-C₆ alkyl-CH═NOY₁, C₁-C₆ alkyl-O—N═C(Y₁)Y₂, phenyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₃ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₃ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy;

Y₁ and Y₂ are independently selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy;

X₃ is selected from hydrogen, cyano, halogen, C₁-C₃ alkylsulfonyl, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ alkoxy C₁-C₃ alkyl, C₁-C₃ alkoxy C₁-C₃ alkoxy, C₁-C₃ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkyloxy;

when X₁ is selected from chlorine and X₃ is selected from methylsulfonyl, X₂ is not 2-thiazolyl;

Z₁ is selected from C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl or phenyl;

Z₂ is selected from H, C₁-C₆ alkyl, C₁-C₆ haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or C₁-C₆ haloalkyl;

Q is selected from Q₁ or Q₂ group;

Q₂ is selected from cycloalkenyl; the hydrogen on the ring may be substituted by the following substituents which are selected from C₁-C₆ alkyl, C₁-C₆ alkoxy or C₁-C₆ alkenyl;

R₁ to R₅ are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy or benzyloxy, wherein

R₁ and R₂ form a benzene ring or a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring;

R₂ and R₃ can form a benzene ring or a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring;

the Q of the above formula I is selected from a stereoisomer of the compound shown by Q₁.

A further preferred compound is: in the formula I:

X₁ is selected from hydrogen, cyano, nitro, halogen, C₁-C₃ alkylsulfonyl, C₁-C₃ alkyl and C₁-C₃ haloalkyl;

W is selected from N or CX₂;

X₂ is selected from hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₃ alkyl, C₃-C₆ halocycloalkyl C₁-C₃ alkyl, Y₁ oxy, Y₁ thio, Y₁Y₂ amino, Y₁ sulfonyl, Y₁ oxy C₁-C₃ alkyl, Y₁ thio C₁-C₃ alkyl, Y₁Y₂ amino C₁-C₃ alkyl, Y₁ sulfonyl C₁-C₃ alkyl, C(O)Y₁, C(O)OY₁, OC(O)OY₁, N(Y₁)C(O)OY₂, C(O)N(Y₁)Y₂, N(Y₁)C(O)N(Y₁)Y₂, OC(O)N(Y₁)Y₂, C(O)N(Y₁)OY₂, N(Y₁)S(O)₂Y₂, N(Y₁)C(O)Y₂, OS(O)₂Y₁, CH═NOY₁, C₁-C₆ alkyl-CH═NOY₁, C₁-C₆ alkyl-O—N═C(Y₁)Y₂, phenyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₃ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₃ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy;

Y₁ and Y₂ are independently selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy;

X₃ is selected from hydrogen, cyano, halogen, C₁-C₃ alkylsulfonyl, C₁-C₃ alkyl and C₁-C₃ haloalkyl;

when X₁ is selected from chlorine and X₃ is selected from methylsulfonyl, X₂ is not 2-thiazolyl;

Z₁ is selected from C₁-C₃ alkyl or phenyl;

Z₂ is selected from H, C₁-C₃ alkyl and C₁-C₃ haloalkyl;

Q is selected from Q₁ or Q₂ group;

Q₂ is selected from G1, G2, G3, G4, G5 or G6 group;

R₁ to R₅ are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, methyl, ethyl, propyl, vinyl, propenyl, ethynyl, propynyl, methoxy, ethoxyl, benzyloxy, trifluoromethyl or trifluoromethoxy;

R₁ and R₂ are selected from a benzene ring formed together with the carbon atoms on the connected benzene ring;

R₂ and R₃ are selected from a benzene ring, 1,3-dioxane ring or 1,4-dioxane ring formed together with the carbon atoms on the connected benzene ring;

the Q of the above formula I is selected from a trans-stereoisomer of the compound shown by Q₁.

In the definitions of the compounds of the formula I provided above, the terms used in the collection are defined as follows:

Alkyl refers to linear or branched groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl and n-hexyl and so on. Cycloalkyl refers to groups in the form of cyclic chain, such as cyclopropyl, methylcyclopropyl, cyclopropylcyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl and so on. Alkenyl refers to linear or branched alkenyl, such as vinyl, 1-propenyl, 2-propenyl, butenyl, pentenyl and hexenyl and so on. Alkynyl refers to linear or branched chain alkynyl, such as 1-propynyl, 2-propynyl, butynyl, pentynyl and hexynyl and so on. Alkoxy refers to a group having an oxygen atom at the end of the alkyl, such as methoxy, ethoxy, n-propoxy, isopropoxy and tert-butoxy and so on. The 5-7-membered heterocycle containing 1-4 heteroatoms refers to a 5-7-membered heterocyclic compound containing 1-4 heteroatoms without aromatic characteristics, such as ethylene oxide, tetrahydrofuran, imidazolinone, caprolactam, 1,3-dioxane ring and 1,4-dioxane ring and so on. The 5-7-membered aromatic heterocycle containing 1-4 heteroatoms refers to a 5-7-membered heterocyclic compound containing 1-4 heteroatoms having aromatic characteristics, such as furan, thiophene, pyrazole and pyridine and so on. Stereoisomers mean that hydrogen atoms on the carbon-carbon double bond B in the formula I are on the same side (cis) or on both sides (trans) of the bond B.

The compound of the formula I in the present invention can be prepared by the following method:

The compound of the formula II and the compound of the formula III react in a suitable solvent at temperature of −10° C. to a boiling point of the suitable solvent for 0.5-48 hours to obtain a target compound I. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethylsulfoxide and so on.

Addition of a suitable alkali substance can be beneficial to the reaction. The suitable alkali is selected from organic alkali such as triethylamine, N, N-dimethylaniline or pyridine and so on, or inorganic alkali such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide and so on.

The compound of the formula III can be prepared from the corresponding acid (commercially available) by reference to Modern Agrochemicals 10(5), 16-20, 23; 2011.

The preparation method of the compound of the formula II is as follows:

The compound of the formula IV reacts under the action of alkali and catalyst in a suitable solvent at temperature of −10° C. to a boiling point of the suitable solvent for 0.5-48 hours to obtain a compound of formula II. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethylsulfoxide and so on. Proper alkali is selected from sodium carbonate, potassium carbonate or triethylamine and so on. A proper catalyst is selected from sodium carbonate, potassium carbonate, acetone cyanohydrin, azide, azide quaternary ammonium salt, metal cyanide or DMAP and so on.

The preparation method of the compound of the formula IV is as follows:

The compound of the formula V and the compound of the formula VI (commercially available or prepared by the method described in reference EP0240001) react in a suitable solvent at temperature of −10° C. to a boiling point of the suitable solvent for 0.5-24 hours to obtain the compound of the formula IV. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethylsulfoxide and so on.

Addition of a suitable alkali substance can be beneficial to the reaction. The suitable alkali is selected from organic alkali such as triethylamine, N, N-dimethylaniline or pyridine and so on, or inorganic alkali such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide and so on.

The corresponding raw material carboxylic acid (commercially available) of the compound of the formula V and an acyl halide reagent react in a suitable solvent at temperature of −10° C. to a boiling point of the suitable solvent for 0.5-48 hours to obtain the compound of the formula V. The acyl halide reagent is selected from oxalyl chloride, thionyl chloride, phosphorous oxychloride, phosphorus trichloride or phosphorus pentachloride and so on. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, hexane, benzene, toluene, acetonitrile, acetic acid, dioxane or liquid acyl halide reagent and so on.

The compound of the formula I of the present invention and the stereoisomer thereof or the compound of the formula I and the agriculturally acceptable salt of the isomer have herbicidal activity and can be used for agriculturally controlling various weeds.

The present invention also comprises a herbicidal composition using the compound of the formula I and the stereoisomer thereof or the compound of the formula I and the agriculturally acceptable salt of the isomer as active ingredients. The weight percentage of the active ingredient in the herbicidal composition is 1-99%. The herbicidal composition also comprises an agriculturally acceptable carrier.

The herbicidal composition of the present invention can be applied in the forms of various formulations. The compound of the present invention is generally dissolved or dispersed in the carrier and prepared into the formulation for easier dispersion when used as a herbicide. For example, the chemical formulations can be prepared into wettable powder or missible oil. Therefore, in the compositions, at least one liquid or solid carrier is added, and generally a suitable surfactant needs to be added.

The present invention also provides an implementing method for controlling weeds. The method comprises applying an effective dose of the herbicidal composition of the present invention to the weed or a weed growing place or a surface of a growth medium thereof. A suitable effective dose is 1 to 1000 grams per hectare, and a preferred effective dose is 10 to 500 grams per hectare. For some applications, one or more other herbicides can be added to the herbicidal composition of the present invention, thereby generating additional advantages and effects.

The compound of the present invention can be used alone or in combination with other known pesticides, bactericides, plant growth regulators or fertilizers.

Compared with the prior art, the alkene-containing carboxylate compound of the present invention not only has excellent herbicidal activity, but also is safe for crops.

It should be clear that various changes and modifications can be made within the scope defined by the claims of the present invention.

DETAILED DESCRIPTION

The following examples and biometric test results can be used to further illustrate the present invention, but are not intended to limit the present invention.

Synthesis Example Embodiment 1 Synthesis of Compound 1-1 (1) Synthesis of 2-methanesulfonyl-4-trifluoromethyl benzoyl chloride

2-methanesulfonyl-4-trifluoromethylbenzoic acid (30 g, 112 mmol) and toluene (200 ml) were added to a reaction flask; thionyl chloride (53 g, 447 mmol) was slowly added; the mixture was heated and refluxed for 4 hours; and the solvent was evaporated under reduced pressure to obtain 32 g of yellow solid, which is directly used in the next step.

(2) Synthesis of 2-methanesulfonyl-4-trifluoromethyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester

1,3-dimethyl-5-hydroxypyrazole (13 g, 112 mmol), 1,2-dichloroethane (200 ml) and triethylamine (34 g, 336 mmol) were added to the reaction flask, and the 1,2-dichloroethane solution (100 ml) of 2-methanesulfonyl-4-trifluoromethyl benzoyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (1000 ml) was added to the residue; water (500 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (500 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 28 g of yellow solid, with a yield of 68%.

(3) Synthesis of 1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole

2-methanesulfonyl-4-trifluoromethyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester (6 g, 16.6 mmol), 1,2-dichloroethane (50 ml), triethylamine (15 g, 148 mmol) and acetone cyanohydrin (1 ml) were added to the reaction flask; the mixture was kept at 60° C. to react for 6 hours and cooled to room temperature; water (100 ml) was added to the reaction solution, and shaken thoroughly and layered; the pH of the aqueous phase was adjusted to be 2-3 with 20% hydrochloric acid, and the aqueous phase was extracted twice with ethyl acetate (100 ml). The organic phase was washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; and the solvent was evaporated under reduced pressure to obtain 5.4 g of red oil with a yield of 90%.

(4) Synthesis of Cinnamyl Chloride

Cinnamic acid (0.17 g, 1.1 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (0.7 g, 5.5 mmol) was slowly added; the mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 0.18 g of pale yellow solid which was used directly in the next step.

(5) Synthesis of Compound 1-1

1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml) of cinnamyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.35 g of white solid compound 1, with a purity of 99.3% and a yield of 64%.

Embodiment 2 Synthesis of Compound 1-7 (1) Synthesis of 3,4-(methylenedioxy) cinnamyl Chloride

3,4-(methylenedioxy) cinnamic acid (0.21 g, 1.1 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (0.7 g, 5.5 mmol) was slowly added; the mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 0.23 g of pale yellow solid which was used directly in the next step.

(2) Synthesis of Compound 1-7

1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol, see step 3 of embodiment 1 for preparation), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml) of 3,4-(methylenedioxy) cinnamyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.38 g of pale yellow solid compound 7, with a purity of 94.6% and a yield of 60.7%.

Embodiment 3 Synthesis of Compound 2-379 (1) Synthesis of 1-cyclohexenoyl Chloride

1-cyclohexenoic acid (0.14 g, 1.1 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (0.7 g, 5.5 mmol) was slowly added; the mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 0.16 g of pale yellow solid which was used directly in the next step.

(2) Synthesis of Compound 2-379

1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol, see step 3 of embodiment 1 for preparation), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml) of 1-cyclohexenoyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent is evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.4 g of off-white solid compound 2-379, with a purity of 99.4% and a yield of 77.1%.

Embodiment 4 Synthesis of Compound 1-16 (1) Synthesis of 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl chloride

2-methanesulfonyl-4-trifluoromethylbenzoic acid (4 g, 14.35 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (9.11 g, 71.8 mmol) was slowly added; the mixture was stirred at room temperature for 40 minutes; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 4.26 g of yellow solid which was used directly in the next step.

(2) Synthesis of 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester

1,3-dimethyl-5-hydroxypyrazole (1.77 g, 15.79 mmol), dichloroethane (100 ml) and triethylamine (2.9 g, 28.7 mmol) were added to the reaction flask, and the dichloroethane solution (30 ml) of 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (1000 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (100 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 3.4 g of off-white solid, with a yield of 63.5%.

(3) Synthesis of 1,3-dimethyl-4-(2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl)-5-hydroxypyrazole

2-chloro-3-methoxymethyl-4-methylsulfonyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester (3.4 g, 9.12 mmol), dichloromethane (100 ml), triethylamine (1.38 g, 13.68 mmol) and acetone cyanohydrin (1 ml) were added to the reaction flask to react at room temperature for 12 hours; and water extraction (50 ml (3)) was added to the reaction solution. After the aqueous phase was collected, the pH was adjusted to be 2-3 with 20% hydrochloric acid, and the aqueous phase was extracted twice with ethyl acetate (100 ml). The organic phase was washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; and the solvent was evaporated under reduced pressure to obtain 3.26 g of yellow solid with a yield of 96%.

(4) Synthesis of Compound 1-16

1,3-dimethyl-4-(2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl)-5-hydroxypyrazole (0.4 g, 1.07 mmol), dichloromethane (20 ml) and triethylamine (0.22 g, 2.15 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml, see step 4 of embodiment 1 for preparation) of cinnamyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.31 g of white solid compound 16, with a purity of 93.2% and a yield of 53.5%.

Embodiment 5 Synthesis of Compound 2-307

1,3-dimethyl-4-(2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol, see step 3 of embodiment 4 for preparation), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution of 1-cyclohexene-1-acyl chloride (0.2 g of 1.1 mmol 1-cyclohexene-1-acyl chloride was dissolved in 15 ml of dichloromethane, see step 1 of embodiment 3 for preparation) was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.45 g of white solid, with a purity of 99.6% and a yield of 87%.

The initial substances are replaced according to the above recorded method to obtain other compounds shown by the formula I. Part of the compounds of the formula I can be found in Table 1, Table 2, Table 3 and Table 4, wherein in Table 1 and Table 2, W is selected from CX₂ and the stereo configuration in Table 1 is trans; in Table 3 and Table 4, W is selected from N and the stereo configuration in Table 3 is trans.

In the compound of the formula I, W is CX₂ and the stereo configuration is trans.

TABLE 1 Structures and Physical Properties of Part of Compounds of Formula 1 Appearance Com- (Melting pound X₁ X₂ X₃ Z₁ Z₂ R₁ R₂ R₃ R₄ R₅ Point° C.) 1-1 SO₂CH₃ H CF₃ CH₃ CH₃ H H H H H white solid (144-146) 1-2 SO₂CH₃ H CF₃ CH₃ CH₃ Cl H Cl H H 1-3 SO₂CH₃ H CF₃ CH₃ CH₃ H H OCH₃ H H 1-4 SO₂CH₃ H CF₃ CH₃ CH₃ H H NO₂ H H 1-5 SO₂CH₃ H CF₅ CH₃ CH₃ H H CH₃ H H 1-6 SO₂CH₃ H CF₃ CH₃ CH₃ H H

H H 1-7 SO₂CH₃ H CF₃ CH₃ CH₃ H

H H pale yellow solid (99-101) 1-8 SO₂CH₃ H CF₃ CH₃ CH₃ H

H H 1-9 SO₂CH₃ H CF₅ CH₃ CH₃ H

H H 1-10 SO₂CH₃ H CF₃ CH₃ CH₃

H H H 1-11 SO₂CH₃ H CF₃ CH₃ CF₃ H H H H H 1-12 SO₂CH₃ H CF₃ CH₃ H H H H H H 1-13 SO₂CH₃ H CF₃ CH₃ CH₂CH₃ H H H H H 1-14 SO₂CH₃ H CF₃

CH₃ H H H H H 1-15 SO₂CH₃ H CF₃ CH₃

H H H H H 1-16 Cl

SO₂CH₃ CH₃ CH₃ H H H H H white solid (139-141) 1-17 Cl

SO₂CH₃ CH₃ CH₃ Cl H Cl H H 1-18 Cl

SO₂CH₃ CH₃ CH₃ H H OCH₃ H H white solid (151-153) 1-19 Cl

SO₂CH₃ CH₃ CH₃ H H NO₂ H H 1-20 Cl

SO₂CH₃ CH₃ CH₃ H H CF₃ H H white solid (139-141) 1-21 Cl

SO₂CH₃ CH₃ CH₃ H H

H H pale pink solid (195-197) 1-22 Cl

SO₂CH₃ CH₃ CH₃ H

H H pale yellow solid (160-162) 1-23 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-24 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-25 Cl

SO₂CH₃ CH₃ CH₃

H H H 1-26 Cl

SO2CH₃ CH₃ CF₃ H H H H H 1-27 Cl

SO₂CH₃ CH₃ H H H H H H 1-28 Cl

SO₂CH₃ CH₃ CH₂CH₃ H H H H H 1-29 Cl

SO₂CH₃

CH₃ H H H H H U 1-30 Cl

SO₂CH₃ CH₃

H H H H H 1-31 Cl CH₃ SO₂CH₃ CH₃ CH₃ H H H H H pale yellow solid (199-201) 1-32 Cl CH₃ SO₂CH₃ CH₃ CH₃ Cl H Cl H H 1-33 Cl CH₃ CO₂CH₃ CH₃ CH₃ H H OCH₃ H H 1-34 Cl CH₃ SO₂CH₃ CH₃ CH₃ H H NO₃ H H 1-35 Cl CH₃ SO₂CH₃ CH₃ CH₃ H H CF₃ H H 1-36 Cl CH₃ SO₂CH₃ CH₃ CH₃ H H

H H 1-37 Cl CH₃ SO₂CH₃ CH₃ CH₃ H

H H white solid (227-229) 1-38 Cl CH₃ SO₂CH₃ CH₃ CH₃ H

H H 1-39 Cl CH₃ SO₂CH₃ CH₃ CH₃ H

H H 1-40 Cl CH₃ SO₂CH₃ CH₃ CH₃

H H H 1-41 Cl CH₃ SO₂CH₃ CH₃ CF₃ H H H H H 1-42 Cl CH₃ SO₂CH₃ CH₃ H H

H H yellow solid (151-152) 1-43 Cl CH₃ SO₂CH₃ CH₃ CH₂CH₃ H H H H H 1-44 Cl CH₃ SO₂CH₃

CH₃ H H H H H 1-45 Cl CH₃ SO.CH, CH₃

H H H H H 1-46 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-47 Cl

SO₂CH₃ CH₃ CH₃ Cl H Cl H H 1-48 Cl

SO₂CH₃ CH₃ CH₃ H H OCH₃ H H 1-49 Cl

SO₂CH₃ CH₃ CH₃ H H NO₂ H H 1-50 Cl

SO₂CH₃ CH₃ CH₃ H H CF₃ H H 1-51 Cl

SO₂CH₃ CH₃ CH₃ H H

H H 1-52 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-53 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-54 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-55 Cl

SO₂CH₃ CH₃ CH₃

H H H 1-56 Cl

SO₂CH₃ CH₃ CF₃ H H H H H 1-57 Cl

SO₂CH₃ CH₃ H H H H H H 1-58 Cl

SO₂CH₃ CH₃ CH₂CH₃ H H H H H 1-59 Cl

SO₂CH₃

CH₃ H H H H H 1-60 Cl

SO₂CH₃ CH₃

H H H H H 1-61 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-62 Cl

SO₂CH₃ CH₃ CH₃ Cl H Cl H H 1-63 Cl

SO₂CH₃ CH₃ CH₃ H H OCH₃ H H 1-64 Cl

SO₂CH₃ CH₃ CH₃ H H NO₂ H H 1-65 Cl

SO₂CH₃ CH₃ CH₃ H H CF₃ H H 1-66 Cl

SO₂CH₃ CH₃ CH₃ H H

H H 1-67 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-68 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-69 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-70 Cl

SO₂CH₃ CH₃ CH₃

H H H 1-71 Cl

SO₂CH₃ CH₃ CF₃ H H H H H 1-72 Cl

SO₂CH₃ CH₃ H H H H H H 1-73 Cl

SO₂CH₃ CH₃ CH₂CH₃ H H H H H 1-74 Cl

SO₂CH₃

CH₃ H H H H H 1-75 Cl

SO₂CH₃ CH₃

H H H H H 1-76 Cl

SO₂CH₃ CH₃ CH₃ H H H H H white solid (123-125) 1-77 Cl

SO₂CH₃ CH₃ CH₃ Cl H Cl H H 1-78 Cl

SO₂CH₃ CH₃ CH₃ H H OCH₃ H H 1-79 Cl

SO₂CH₃ CH₃ CH₃ H H NO₂ H H 1-80 Cl

SO₂CH₃ CH₃ CH₃ H H CF₃ H H 1-81 Cl

SO₂CH₃ CH₃ CH₃ H H

H H yellow solid (135-136) 1-82 Cl

SO₂CH₃ CH₃ CH₃ H

H H yellow solid (87-88) 1-83 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-84 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-85 Cl

SO₂CH₃ CH₃ CH₃

H H H 1-86 Cl

SO₂CH₃ CH₃ CF₃ H H H H H 1-87 Cl

SO₂CH₃ CH₃ H H H H H H 1-88 Cl

SO₂CH₃ CH₃ CH₂CH₃ H H H H H 1-89 Cl

SO₂CH₃

CH₃ H H H H H 1-90 Cl

SO₂CH₃ CH₃

H H H H H 1-91 Cl CH₂Br SO₂CH₃ CH₃ CH₃ H H H H H 1-92 Cl CH₂Br SO₂CH₃

CH₃ H H H H H 1-93 Cl CH₂Br SO₂CH₃ CH₃

H H H H H 1-94 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-95 Cl

SO₂CH₃

CH₃ H H H H H 1-96 Cl

SO₂CH₃ CH₃

H H H H H 1-97 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-98 Cl

SO₂CH₃

CH₃ H H H H H 1-99 Cl

SO₂CH₃ CH₃

H H H H H 1-100 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-101 Cl

SO₂CH₃

CH₃ H H H H H 1-102 Cl

SO₂CH₃ CH₃

H H H H H 1-103 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-104 Cl

SO₂CH₃

CH₃ H H H H H 1-105 Cl

SO₂CH₃ CH₃

H H H H H 1-106 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-107 Cl

SO₂CH₃

CH₃ H H H H H 1-108 Cl

SO₂CH₃ CH₃

H H H H H 1-109 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-110 Cl

SO₂CH₃

CH₃ H H H H H 1-111 Cl

SO₂CH₃ CH₃

H H H H H 1-112 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-113 Cl

SO₂CH₃

CH₃ H H H H H 1-114 Cl

SO₂CH₃ CH₃

H H H H H 1-115 Cl

SO₂CH₃ CH₃ CH₃ H H H H H pale yellow oil 1-116 Cl

SO₂CH₃

CH₃ H H H H H 1-117 Cl

SO₂CH₃ CH₃

H H H H H 1-118 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-119 Cl

SO₂CH₃

CH₃ H H H H H 1-120 Cl

SO₂CH₃ CH₃

H H H H H 1-121 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-122 Cl

SO₂CH₃

CH₃ H H H H H 1-123 Cl

SO₂CH₃ CH₃

H H H H H 1-124 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-125 Cl

SO₂CH₃

CH₃ H H H H H 1-126 Cl

SO₂CH₃ CH₃

H H H H H 1-127 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-128 Cl

SO₂CH₃

CH₃ H H H H H 1-129 Cl

SO₂CH₃ CH₃

H H H H H 1-130 Cl SO₂CH₃ SO₂CH₃ CH₃ CH₃ H H H H H 1-131 Cl SO₂CH₃ SO₂CH₃

CH₃ H H H H H 1-132 Cl SO₂CH₃ SO₂CH₃ CH₃

H H H H H 1-133 Cl SO₂CH₃ CF₃ CH₃ CH₃ H H H H H 1-134 Cl SO₂CH₃ CF₃

CH₃ H H H H H 1-135 Cl SO₂CH₃ CF₃ CH₃

H H H H H 1-136 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-137 Cl

SO₂CH₃

CH₃ H H H H H 1-138 Cl

SO₂CH₃ CH₃

H H H H H 1-139 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-140 Cl

SO₂CH₃

CH₃ H H H H H 1-141 Cl

SO₂CH₃ CH₃

H H H H H 1-142 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-143 Cl

SO₂CH₃

CH₃ H H H H H 1-144 Cl

SO₂CH₃ CH₃

H H H H H 1-145 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-146 Cl

SO₂CH₃

CH₃ H H H H H 1-147 Cl

SO₂CH₃ CH₃

H H H H H 1-148 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-149 Cl

SO₂CH₃

CH₃ H H H H H 1-150 Cl

SO₂CH₃ CH₃

H H H H H 1-151 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-152 Cl

SO₂CH₃

CH₃ H H H H H 1-153 Cl

SO₂CH₃ CH₃

H H H H H 1-154 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-155 Cl

SO₂CH₃

CH₃ H H H H H 1-156 Cl

SO₂CH₃ CH₃

H H H H H 1-157 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-158 Cl

SO₂CH₃

CH₃ H H H H H 1-159 Cl

SO₂CH₃ CH₃

H H H H H 1-160 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-161 Cl

SO₂CH₃

CH₃ H H H H H 1-162 Cl

SO₂CH₃ CH₃

H H H H H 1-163 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-164 Cl

SO₂CH₃

CH₃ H H H H H 1-165 Cl

SO₂CH₃ CH₃

H H H H H 1-166 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-167 Cl

SO₂CH₃

CH₃ H H H H H 1-168 Cl

SO₂CH₃ CH₃

H H H H H 1-169 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-170 Cl

SO₂CH₃

CH₃ H H H H H 1-171 Cl

SO₂CH₃ CH₃

H H H H H 1-172 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-173 Cl

SO₂CH₃

CH₃ H H H H H 1-174 Cl

SO₂CH₃ CH₃

H H H H H 1-175 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-176 Cl

SO₂CH₃

CH₃ H H H H H 1-177 Cl

SO₂CH₃ CH₃

H H H H H 1-178 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-179 Cl

SO₂CH₃

CH₃ H H H H H 1-180 Cl

SO₂CH₃ CH₃

H H H H H 1-181 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-182 Cl

SO₂CH₃

CH₃ H H H H H 1-183 Cl

SO₂CH₃ CH₃

H H H H H 1-184 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-185 Cl

SO₂CH₃

CH₃ H H H H H 1-186 Cl

SO₂CH₃ CH₃

H H H H H 1-187 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-188 Cl

SO₂CH₃

CH₃ H H H H H 1-189 Cl

SO₂CH₃ CH₃

H H H H H 1-190 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-191 Cl

SO₂CH₃

CH₃ H H H H H 1-192 Cl

SO₂CH₃ CH₃

H H H H H 1-193 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-194 Cl

SO₂CH₃

CH₃ H H H H H 1-195 Cl

SO₂CH₃ CH₃

H H H H H 1-196 Cl CN SO₂CH₃ CH₃ CH₃ H H H H H 1-197 Cl CN SO₂CH₃

CH₃ H H H H H 1-198 Cl CN SO₂CH₃ CH₃

H H H H H 1-199 Cl NO₂ SO₂CH₃ CH₃ CH₃ H H H H H 1-200 Cl NO₂ SO₂CH₃

CH₃ H H H H H 1-201 Cl NO₂ SO₂CH₃ CH₃

H H H H H 1-202 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-203 Cl

SO₂CH₃

CH₃ H H H H H 1-204 Cl

SO₂CH₃ CH₃

H H H H H 1-205 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-206 Cl

SO₂CH₃

CH₃ H H H H H 1-207 Cl

SO₂CH₃ CH₃

H H H H H 1-208 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-209 Cl

SO₂CH₃

CH₃ H H H H H 1-210 Cl

SO₂CH₃ CH₃

H H H H H 1-211 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-212 Cl

SO₂CH₃

CH₃ H H H H H 1-213 Cl

SO₂CH₃ CH₃

H H H H H 1-214 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-215 Cl

SO₂CH₃

CH₃ H H H H H 1-216 Cl

SO₂CH₃ CH₃

H H H H H 1-217 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-218 Cl

SO₂CH₃

CH₃ H H H H H 1-219 Cl

SO₂CH₃ CH₃

H H H H H 1-220 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-221 Cl

SO₂CH₃

CH₃ H H H H H 1-222 Cl

SO₂CH₃ CH₃

H H H H H 1-223 Cl H SO₂CH₃ CH₃ CH₃ H H H H H white solid (150-152) 1-224 Cl H SO₂CH₃

CH₃ H H H H H 1-225 Cl H SO₂CH₃ CH₃

H H H H H 1-226 Cl H SO₂CH₃ CH₃ CH₃ H

H H pale yellow solid (185-187) 1-227 Cl H SO₂CH₃

CH₃ H

H H 1-228 Cl H SO₂CH₃ CH₃

H

H H 1-229 Cl H Cl CH₃ CH₃ H H H H H pale yellow solid (95-97) 1-230 Cl H Cl

CH₃ H H H H H 1-231 Cl H Cl CH₃

H H H H H 1-232 Cl H Cl CH₃ CH₃ H

H H pale yellow solid (114-116) 1-233 Cl H Cl

CH₃ H

H H 1-234 Cl H Cl CH₃

H

H H 1-235 NO₂ H SO₂CH₃ CH₃ CH₃ H H H H H orange solid (196-198) 1-236 NO₂ H SO₂CH₃

CH₃ H H H H H 1-237 NO₂ H SO₂CH₃ CH₃

H H H H H 1-238 NO₂ H SO₂CH₃ CH₃ CH₃ H

H H yellow solid (173-175) 1-239 NO₂ H SO₂CH₃

CH₃ H

H H 1-240 NO₂ H SO₂CH₃ CH₃

H

H H 1-241 Cl Cl SO₂CH₃ CH₃ CH₃ H H H H H 1-242 Cl Cl SO₂CH₃

CH₃ H H H H H 1-243 Cl Cl SO₂CH₃ CH₃

H H H H H 1-244 Cl Cl SO₂CH₃ CH₃ CH₃ H

H H 1-245 Cl Cl SO₂CH₃

CH₃ H

H H 1-246 Cl Cl SO₂CH₃ CH₃

H

H H 1-247 Cl

SO₂CH₃ CH₃ CH₃ H H H H H 1-248 Cl

SO₂CH₃

CH₃ H H H H H 1-249 Cl

SO₂CH₃ CH₃

H H H H H 1-250 Cl

SO₂CH₃ CH₃ CH₃ H

H H 1-251 Cl

SO₂CH₃

CH₃ H

H H 1-252 Cl

SO₂CH₃ CH₃

H

H H 1-253 Cl

SO₂CH₃ CH₃ CH₃ H H H H 1-254 Cl

SO₂CH₃

CH₃ H H H H 1-255 Cl

SO₂CH₃ CH₃

H H H H 1-256 Cl

SO₂CH₃ CH₃ CH₃ H H H H 1-257 Cl

SO₂CH₃

CH₃ H H H H 1-258 Cl

SO₂CH₃ CH₃

H H H H 1-259 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H pale yellow solid (70-72) 1-260 CH₃

SO₂CH₃

CH₃ H H H H H 1-261 SO₂CH₃

SO₂CH₃ CH₃

H H H H H 1-262 CH₃

SO₂CH₃ CH₃ CH₃ H

H H pale yellow solid (134-136) 1-263 CH₃

SO₂CH₃

CH₃ H

H H 1-264 CH₃

SO₂CH₃ CH₃

H

H H 1-265 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H white solid (187-188) 1-266 CH₃

SO₂CH₃

CH₃ H H H H H 1-267 CH₃

SO₂CH₃ CH₃

H H H H H 1-268 CH₃ CH₃ SO₂CH₃ CH₃ CH₃ H H H H H white solid (191-193) 1-269 CH₃ CH₃ SO₂CH₃

CH₃ H H H H H 1-270 CH₃ CH₃ SO₂CH₃ CH₃

H H H H H 1-271 CH₃ CH₂Br SO₂CH₃ CH₃ CH₃ H H H H H 1-272 CH₃ CH₂Br SO₂CH₃

CH₃ H H H H H 1-273 CH₃ CH₂Br SO₂CH₃ CH₃

H H H H H 1-274 CH₃ F SO₂CH₃ CH₃ CH₃ H H H H H 1-275 CH₃ F SO₂CH₃

CH₃ H H H H H 1-276 CH₃ F SO₂CH₃ CH₃

H H H H H 1-277 CH₃ Br SO₂CH₃ CH₃ CH₃ H H H H H 1-278 CH₃ Br SO₂CH₃

CH₃ H H H H H 1-279 CH₃ Br SO₂CH₃ CH₃

H H H H H 1-280 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H pale yellow solid (152-154) 1-281 CH₃

SO₂CH₃

CH₃ H H H H H 1-282 CH₃

SO₂CH₃ CH₃

H H H H H 1-283 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-284 CH₃

SO₂CH₃

CH₃ H H H H H 1-285 CH₃

SO₂CH₃ CH₃

H H H H H 1-286 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-287 CH₃

SO₂CH₃

CH₃ H H H H H I 1-288 CH₃

SO₂CH₃ CH₃

H H H H H 1-289 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-290 CH₃

SO₂CH₃

CH₃ H H H H H 1-291 CH₃

SO₂CH₃ CH₃

H H H H H 1-292 CH₃

SO₂CH₃ CH₃ H H H H H H off- white solid (118-120) 1-293 CH₃

SO₂CH₃

CH, H H H H H 1-294 CH₃

SO₂CH₃ CH₃

H H H H H 1-295 CN

SO₂CH₃ CH₃ CH₃ H H H H H 1-296 CN

SO₂CH₃

CH₃ H H H H H 1-297 CN

SO₂CH₃ CH₃

H H H H H 1-298 CF₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-299 CF₃

SO₂CH₃

CH₃ H H H H H 1-300 CF₃

SO₂CH₃ CH₃

H H H H H 1-301

SO₂CH₃ CH₃ CH₃ H H H H H 1-302

SO₂CH₃

CH₃ H H H H H 1-303

SO₂CH₃ CH₃

H H H H H 1-304

SO₂CH₃ CH₃ CH₃ H H H H H 1-305

SO₂CH₃

CH₃ H H H H H 1-306

SO₂CH₃ CH₃

H H H H H 1-307

SO₂CH₃ CH₃ CH₃ H H H H H 1-308

SO₂CH₃

CH₃ H H H H H 1-309

SO₂CH₃ CH₃

H H H H H 1-310

SO₂CH₃ CH₃ CH₃ H H H H H 1-311

SO₂CH₃

CH₃ H H H H H 1-312

SO₂CH₃ CH₃

H H H H H 1-313

SO₂CH₃ CH₃ CH₃ H H H H H 1-314

SO₂CH₃

CH₃ H H H H H 1-315

SO₂CH₃ CH₃

H H H H H 1-316

SO₂CH₃ CH₃ CH₃ H H H H H 1-317

SO₂CH₃

CH₃ H H H H H 1-318

SO₂CH₃ CH₃

H H H H H 1-319

SO₂CH₃ CH₃ CH₃ H H H H H 1-320

SO₂CH₃

CH₃ H H H H H 1-321

SO₂CH₃ CH₃

H H H H H 1-322 SO₂CH═CH,

SO₂CH₃ CH₃ CH₃ H H H H H 1-323 SO₂CH═CH,

SO₂CH₃

CH₃ H H H H H 1-324 SO₂CH═CH

SO₂CH₃ CH₃

H H H H H 1-325

SO₂CH₃ CH₃ CH₃ H H H H H 1-326

SO₂CH₃

CH₃ H H H H H 1-327

SO₂CH₃ CH₃

H H H H H 1-328

SO₂CH₃ CH₃ CH₃ H H H H H 1-329

SO₂CH₃

CH₃ H H H H H 1-330

SO₂CH₃ CH₃

H H H H H 1-331

SO₂CH₃ CH₃ CH₃ H H H H H 1-332

SO₂CH₃

CH₃ H H H H H 1-333

SO₂CH₃ CH₃

H H H H H 1-334

SO₂CH₃ CH₃ CH₃ H H H H H 1-335

SO₂CH₃

CH₃ H H H H H 1-336

SO₂CH₃ CH₃

H H H H H 1-337

SO₂CH₃ CH₃ CH₃ H H H H H 1-338

SO₂CH₃

CH₃ H H H H H 1-339

SO₂CH₃ CH₃

H H H H H 1-340

SO₂CH₃ CH₃ CH₃ H H H H H 1-341

SO₂CH₃

CH₃ H H H H H 1-342

SO₂CH₃ CH₃

H H H H H 1-343

SO₂CH₃ CH₃ CH₃ H H H H H 1-344

SO₂CH₃

CH₃ H H H H H 1-345

SO₂CH₃ CH₃

H H H H H 1-346 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H white solid (135-137) 1-347 CH₃

SO₂CH₃

CH₃ H H H H H 1-348 CH₃

SO₂CH₃ CH₃

H H H H H 1-349 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H yellow oil 1-350 CH₃

SO₂CH₃

CH₃ H H H H H 1-351 CH₃

SO₂CH₃ CH₃

H H H H H 1-352 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-353 CH₃

SO₂CH₃

CH₃ H H H H H 1-354 CH₃

SO₂CH₃ CH₃

H H H H H 1-355 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-356 CH₃

SO₂CH₃

CH₃ H H H H H 1-357 CH₃

SO₂CH₃ CH₃

H H H H H 1-358 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-359 CH₃

SO₂CH₃

CH₃ H H H H H 1-360 CH₃

SO₂CH₃ CH₃

H H H H H 1-361 CH₃ SO₂CH₃ CF₃ CH₃ CH₃ H H H H H 1-362 CH₃ SO₂CH₃ CF₃

CH₃ H H H H H 1-363 CH₃ SO₂CH₃ CF₃ CH₃

H H H H H 1-364 CH₃

SO₂CH₃ CH₃ CH₃ H H H H H 1-365 CH₃

SO₂CH₃

CH₃ H H H H H 1-366 CH₃

SO₂CH₃ CH₃

H H H H H 1-367 NO₂ H Cl CH₃ CH₃ H H H H H orange solid (107-109) 1-368 NO₂ H Cl

CH₃ H H H H H 1-369 NO₂ H Cl CH₃

H H H H H 1-370 CH₃

SO₂CH₃ CH₃ CH₃ H H OCH₃ H H yellow oil 1-371 SO₂CH₃ H Cl CH₃ CH₃ H H H H H white solid (153-154) 1-372 CH₃

SO₂CH₃ CH₃CH₂ H H H H H H yellow oil 1-373 Cl

SO₂CH₃ CH₃ CH₃ H H H H H yellow oil 1-374 Cl

SO₂CH₃ CH₃ CH₃ H H H H H yellow oil 1-375 Cl

SO₂CH₃ CH₃ CH₃ H H H H H yellow oil 1-376 Cl

SO₂CH₃ CH₃ CH₃ H H H H H pale yellow oil 1-377 Cl

SO₂CH₃ CH₃ CH₃ H H H H H pale yellow oil

In the compound of the formula I, W is CX₂.

TABLE 2 Structures and Physical Properties of Part of Compounds of Formula I Appearance Com- (Melting pound X₁ X₂ X₃ Z₁ Z₂ Q Point ° C.) 2-1 CH₃

SO₂CH₃ CH₃ CH₃

white solid (170-171) 2-2 CH₃

SO₂CH₃ CH₃ CH₃

2-3 CH₃

SO₂CH₃ CH₃ CH₃

2-4 CH₃

SO₂CH₃ CH₃ CH₃

2-5 CH₃

SO₂CH₃ CH₃ CH₃

2-6 CH₃

SO₂CH₃ CH₃ CH₃

2-7 CH₃

SO₂CH₃ CH₃CH₂ H

2-8 CH₃

SO₂CH₃ CH₃CH₂ H

2-9 CH₃

SO₂CH₃ CH₃CH₂ H

2-10 CH₃

SO₂CH₃ CH₃CH₂ H

2-11 CH₃

SO₂CH₃ CH₃CH₂ H

2-12 CH₃

SO₂CH₃ CH₃CH₂ H

2-13 CH₃

SO₂CH₃ CH₃ H

2-14 CH₃

SO₂CH₃ CH₃ H

2-15 CH₃

SO₂CH₃ CH₃ H

2-16 CH₃

SO₂CH₃ CH₃ H

2-17 CH₃

SO₂CH₃ CH₃ H

2-18 CH₃

SO₂CH₃ CH₃ H

2-19 CH₃

SO₂CH₃ CH₃ CH₃

white solid (164-165) 2-20 CH₃

SO₂CH₃ CH₃ CH₃

2-21 CH₃

SO₂CH₃ CH₃ CH₃

2-22 CH₃

SO₂CH₃ CH₃ CH₃

2-23 CH₃

SO₂CH₃ CH₃ CH₃

2-24 CH₃

SO₂CH₃ CH₃ CH₃

2-25 CH₃

SO₂CH₃ CH₂CH₃ H

2-26 CH₃

SO₂CH₃ CH₂CH₃ H

2-27 CH₃

SO₂CH₃ CH₂CH₃ H

2-28 CH₃

SO₂CH₃ CH₂CH₃ H

2-29 CH₃

SO₂CH₃ CH₂CH₃ H

2-30 CH₃

SO₂CH₃ CH₂CH₃ H

2-31 CH₃

SO₂CH₃ CH₃ H

2-32 CH₃

SO₂CH₃ CH₃ H

2-33 CH₃

SO₂CH₃ CH₃ H

2-34 CH₃

SO₂CH₃ CH₃ H

2-35 CH₃

SO₂CH₃ CH₃ H

2-36 CH₃

SO₂CH₃ CH₃ H

2-37 CH₃

SO₂CH₃ CH₃ CH₃

white solid (157-158) 2-38 CH₃

SO₂CH₃ CH₃ CH₃

2-39 CH₃

SO₂CH₃ CH₃ CH₃

2-40 CH₃

SO₂CH₃ CH₃ CH₃

2-41 CH₃

SO₂CH₃ CH₃ CH₃

2-42 CH₃

SO₂CH₃ CH₃ CH₃

2-43 CH₃

SO₂CH₃ CH₃CH₂ H

2-44 CH₃

SO₂CH₃ CH₃CH₂ H

2-45 CH₃

SO₂CH₃ CH₃CH₂ H

2-46 CH₃

SO₂CH₃ CH₃CH₂ H

2-47 CH₃

SO₂CH₃ CH₃CH₂ H

2-48 CH₃

SO₂CH₃ CH₃CH₂ H

2-49 CH₃

SO₂CH₃ CH₃ H

2-50 CH₃

SO₂CH₃ CH₃ H

2-51 CH₃

SO₂CH₃ CH₃ H

2-52 CH₃

SO₂CH₃ CH₃ H

2-53 CH₃

SO₂CH₃ CH₃ H

2-54 CH₃

SO₂CH₃ CH₃ H

2-55 CH₃

SO₂CH₃ CH₃ CH₃

yellow oil 2-56 CH₃

SO₂CH₃ CH₃ CH₃

2-57 CH₃

SO₂CH₃ CH₃ CH₃

pale yellow solid (134-136) 2-58 CH₃

SO₂CH₃ CH₃ CH₃

2-59 CH₃

SO₂CH₃ CH₃ CH₃

2-60 CH₃

SO₂CH₃ CH₃ CH₃

2-61 CH₃

SO₂CH₃ CH₃CH₂ H

yellow oil 2-62 CH₃

SO₂CH₃ CH₃CH₂ H

2-63 CH₃

SO₂CH₃ CH₃CH₂ H

yellow oil 2-64 CH₃

SO₂CH₃ CH₃CH₂ H

2-65 CH₃

SO₂CH₃ CH₃CH₂ H

2-66 CH₃

SO₂CH₃ CH₃CH₂ H

2-67 CH₃

SO₂CH₃ CH₃ H

yellow oil 2-68 CH₃

SO₂CH₃ CH₃ H

2-69 CH₃

SO₂CH₃ CH₃ H

2-70 CH₃

SO₂CH₃ CH₃ H

2-71 CH₃

SO₂CH₃ CH₃ H

2-72 CH₃

SO₂CH₃ CH₃ H

2-73 CH₃

SO₂CH₃ CH₃ CH₃

brown oil 2-74 CH₃

SO₂CH₃ CH₃ CH₃

2-75 CH₃

SO₂CH₃ CH₃ CH₃

2-76 CH₃

SO₂CH₃ CH₃ CH₃

2-77 CH₃

SO₂CH₃ CH₃ CH₃

2-78 CH₃

SO₂CH₃ CH₃ CH₃

2-79 CH₃

SO₂CH₃ CH₃CH₂ H

2-80 CH₃

SO₂CH₃ CH₃CH₂ H

2-81 CH₃

SO₂CH₃ CH₃CH₂ H

2-82 CH₃

SO₂CH₃ CH₃CH₂ H

2-83 CH₃

SO₂CH₃ CH₃CH₂ H

2-84 CH₃

SO₂CH₃ CH₃CH₂ H

2-85 CH₃

SO₂CH₃ CH₃ H

2-86 CH₃

SO₂CH₃ CH₃ H

2-87 CH₃

SO₂CH₃ CH₃ H

2-88 CH₃

SO₂CH₃ CH₃ H

2-89 CH₃

SO₂CH₃ CH₃ H

2-90 CH₃

SO₂CH₃ CH₃ H

2-91 CH₃

SO₂CH₃ CH₃ CH₃

2-92 CH₃

SO₂CH₃ CH₃ CH₃

2-93 CH₃

SO₂CH₃ CH₃ CH₃

2-94 CH₃

SO₂CH₃ CH₃ CH₃

2-95 CH₃

SO₂CH₃ CH₃ CH₃

2-96 CH₃

SO₂CH₃ CH₃ CH₃

2-97 CH₃

SO₂CH₃ CH₃CH₂ H

2-98 CH₃

SO₂CH₃ CH₃CH₂ H

2-99 CH₃

SO₂CH₃ CH₃CH₂ H

2-100 CH₃

SO₂CH₃ CH₃CH₂ H

2-101 CH₃

SO₂CH₃ CH₃CH₂ H

2-102 CH₃

SO₂CH₃ CH₃CH₂ H

2-103 CH₃

SO₂CH₃ CH₃ H

2-104 CH₃

SO₂CH₃ CH₃ H

2-105 CH₃

SO₂CH₃ CH₃ H

2-106 CH₃

SO₂CH₃ CH₃ H

2-107 CH₃

SO₂CH₃ CH₃ H

2-108 CH₃

SO₂CH₃ CH₃ H

2-109 CH₃

SO₂CH₃ CH₃ CH₃

2-110 CH₃

SO₂CH₃ CH₃ CH₃

2-111 CH₃

SO₂CH₃ CH₃ CH₃

2-112 CH₃

SO₂CH₃ CH₃ CH₃

2-113 CH₃

SO₂CH₃ CH₃ CH₃

2-114 CH₃

SO₂CH₃ CH₃ CH₃

2-115 CH₃

SO₂CH₃ CH₃CH₂ H

2-116 CH₃

SO₂CH₃ CH₃CH₂ H

2-117 CH₃

SO₂CH₃ CH₃CH₂ H

2-118 CH₃

SO₂CH₃ CH₃CH₂ H

2-119 CH₃

SO₂CH₃ CH₃CH₂ H

2-120 CH₃

SO₂CH₃ CH₃CH₂ H

2-121 CH₃

SO₂CH₃ CH₃ H

white solid (209-210) 2-122 CH₃

SO₂CH₃ CH₃ H

2-123 CH₃

SO₂CH₃ CH₃ H

white solid (199-200) 2-124 CH₃

SO₂CH₃ CH₃ H

2-125 CH₃

SO₂CH₃ CH₃ H

2-126 CH₃

SO₂CH₃ CH₃ H

2-127 CH₃ CH₃ SO₂CH₃ CH₃ CH₃

white solid (186-188) 2-128 CH₃ CH₃ SO₂CH₃ CH₃ CH₃

2-129 CH₃ CH₃ SO₂CH₃ CH₃ CH₃

2-130 CH₃ CH₃ SO₂CH₃ CH₃ CH₃

2-131 CH₃ CH₃ SO₂CH₃ CH₃ CH₃

2-132 CH₃ CH₃ SO₂CH₃ CH₃ CH₃

2-133 CH₃ CH₃ SO₂CH₃ CH₃CH₂ H

2-134 CH₃ CH₃ SO₂CH₃ CH₃CH₂ H

2-135 CH₃ CH₃ SO₂CH₃ CH₃CH₂ H

2-136 CH₃ CH₃ SO₂CH₃ CH₃CH₂ H

2-137 CH₃ CH₃ SO₂CH₃ CH₃CH₂ H

2-138 CH₃ CH₃ SO₂CH₃ CH₃CH₂ H

2-139 CH₃ CH₃ SO₂CH₃ CH₃ H

2-140 CH₃ CH₃ SO₂CH₃ CH₃ H

2-141 CH₃ CH₃ SO₂CH₃ CH₃ H

2-142 CH₃ CH₃ SO₂CH₃ CH₃ H

2-143 CH₃ CH₃ SO₂CH₃ CH₃ H

2-144 CH₃ CH₃ SO₂CH₃ CH₃ H

2-145 CH₃

SO₂CH₃ CH₃ CH₃

white solid (116-118) 2-146 CH₃

SO₂CH₃ CH₃ CH₃

2-147 CH₃

SO₂CH₃ CH₃ CH₃

2-148 CH₃

SO₂CH₃ CH₃ CH₃

2-149 CH₃

SO₂CH₃ CH₃ CH₃

2-150 CH₃

SO₂CH₃ CH₃ CH₃

2-151 CH₃

SO₂CH₃ CH₂CH₃ H

2-152 CH₃

SO₂CH₃ CH₂CH₃ H

2-153 CH₃

SO₂CH₃ CH₂CH₃ H

2-154 CH₃

SO₂CH₃ CH₂CH₃ H

2-155 CH₃

SO₂CH₃ CH₂CH₃ H

2-156 CH₃

SO₂CH₃ CH₂CH₃ H

2-157 CH₃

SO₂CH₃ CH₃ H

2-158 CH₃

SO₂CH₃ CH₃ H

2-159 CH₃

SO₂CH₃ CH₃ H

2-160 CH₃

SO₂CH₃ CH₃ H

2-161 CH₃

SO₂CH₃ CH₃ H

2-162 CH₃

SO₂CH₃ CH₃ H

2-163 Cl

SO₂CH₃ CH₃ CH₃

2-164 Cl

SO₂CH₃ CH₃ CH₃

2-165 Cl

SO₂CH₃ CH₃ CH₃

2-166 Cl

SO₂CH₃ CH₃ CH₃

2-167 Cl

SO₂CH₃ CH₃ CH₃

2-168 Cl

SO₂CH₃ CH₃ CH₃

2-169 Cl

SO₂CH₃ CH₂CH₃ H

2-170 Cl

SO₂CH₃ CH₂CH₃ H

2-171 Cl

SO₂CH₃ CH₂CH₃ H

2-172 Cl

SO₂CH₃ CH₂CH₃ H

2-173 Cl

SO₂CH₃ CH₂CH₃ H

2-174 Cl

SO₂CH₃ CH₂CH₃ H

2-175 Cl

SO₂CH₃ CH₃ H

2-176 Cl

SO₂CH₃ CH₃ H

2-177 Cl

SO₂CH₃ CH₃ H

2-178 Cl

SO₂CH₃ CH₃ H

2-179 Cl

SO₂CH₃ CH₃ H

2-180 Cl

SO₂CH₃ CH₃ H

2-181 Cl

SO₂CH₃ CH₃ CH₃

2-182 Cl

SO₂CH₃ CH₃ CH₃

2-183 Cl

SO₂CH₃ CH₃ CH₃

2-184 Cl

SO₂CH₃ CH₃ CH₃

2-185 Cl

SO₂CH₃ CH₃ CH₃

2-186 Cl

SO₂CH₃ CH₃ CH₃

2-187 Cl

SO₂CH₃ CH₂CH₃ H

2-188 Cl

SO₂CH₃ CH₂CH₃ H

2-189 Cl

SO₂CH₃ CH₂CH₃ H

2-190 Cl

SO₂CH₃ CH₂CH₃ H

2-191 Cl

SO₂CH₃ CH₂CH₃ H

2-192 Cl

SO₂CH₃ CH₂CH₃ H

2-193 Cl

SO₂CH₃ CH₃ H

2-194 Cl

SO₂CH₃ CH₃ H

2-195 Cl

SO₂CH₃ CH₃ H

2-196 Cl

SO₂CH₃ CH₃ H

2-197 Cl

SO₂CH₃ CH₃ H

2-198 Cl

SO₂CH₃ CH₃ H

2-199 Cl

SO₂CH₃ CH₃ CH₃

2-200 Cl

SO₂CH₃ CH₃ CH₃

2-201 Cl

SO₂CH₃ CH₃ CH₃

2-202 Cl

SO₂CH₃ CH₃ CH₃

2-203 Cl

SO₂CH₃ CH₃ CH₃

2-204 Cl

SO₂CH₃ CH₃ CH₃

2-205 Cl

SO₂CH₃ CH₂CH₃ H

2-206 Cl

SO₂CH₃ CH₂CH₃ H

2-207 Cl

SO₂CH₃ CH₂CH₃ H

2-208 Cl

SO₂CH₃ CH₂CH₃ H

2-209 Cl

SO₂CH₃ CH₂CH₃ H

2-210 Cl

SO₂CH₃ CH₂CH₃ H

2-211 Cl

SO₂CH₃ CH₃ H

2-212 Cl

SO₂CH₃ CH₃ H

2-213 Cl

SO₂CH₃ CH₃ H

2-214 Cl

SO₂CH₃ CH₃ H

2-215 Cl

SO₂CH₃ CH₃ H

2-216 Cl

SO₂CH₃ CH₃ H

2-217 Cl

SO₂CH₃ CH₃ CH₃

2-218 Cl

SO₂CH₃ CH₃ CH₃

2-219 Cl

SO₂CH₃ CH₃ CH₃

2-220 Cl

SO₂CH₃ CH₃ CH₃

2-221 Cl

SO₂CH₃ CH₃ CH₃

2-222 Cl

SO₂CH₃ CH₃ CH₃

2-223 Cl

SO₂CH₃ CH₂CH₃ H

2-224 Cl

SO₂CH₃ CH₂CH₃ H

2-225 Cl

SO₂CH₃ CH₂CH₃ H

2-226 Cl

SO₂CH₃ CH₂CH₃ H

2-227 Cl

SO₂CH₃ CH₂CH₃ H

2-228 Cl

SO₂CH₃ CH₂CH₃ H

2-229 Cl

SO₂CH₃ CH₃ H

2-230 Cl

SO₂CH₃ CH₃ H

2-231 Cl

SO₂CH₃ CH₃ H

2-232 Cl

SO₂CH₃ CH₃ H

2-233 Cl

SO₂CH₃ CH₃ H

2-234 Cl

SO₂CH₃ CH₃ H

2-235 Cl

SO₂CH₃ CH₃ CH₃

2-236 Cl

SO₂CH₃ CH₃ CH₃

2-237 Cl

SO₂CH₃ CH₃ CH₃

2-238 Cl

SO₂CH₃ CH₃ CH₃

2-239 Cl

SO₂CH₃ CH₃ CH₃

2-240 Cl

SO₂CH₃ CH₃ CH₃

2-241 Cl

SO₂CH₃ CH₂CH₃ H

2-242 Cl

SO₂CH₃ CH₂CH₃ H

2-243 Cl

SO₂CH₃ CH₂CH₃ H

2-244 Cl

SO₂CH₃ CH₂CH₃ H

2-245 Cl

SO₂CH₃ CH₂CH₃ H

2-246 Cl

SO₂CH₃ CH₂CH₃ H

2-247 Cl

SO₂CH₃ CH₃ H

2-248 Cl

SO₂CH₃ CH₃ H

2-249 Cl

SO₂CH₃ CH₃ H

2-250 Cl

SO₂CH₃ CH₃ H

2-251 Cl

SO₂CH₃ CH₃ H

2-252 Cl

SO₂CH₃ CH₃ H

2-253 Cl

SO₂CH₃ CH₃ CH₃

2-254 Cl

SO₂CH₃ CH₃ CH₃

2-255 Cl

SO₂CH₃ CH₃ CH₃

2-256 Cl

SO₂CH₃ CH₃ CH₃

2-257 Cl

SO₂CH₃ CH₃ CH₃

2-258 Cl

SO₂CH₃ CH₃ CH₃

2-259 Cl

SO₂CH₃ CH₂CH₃ H

2-260 Cl

SO₂CH₃ CH₂CH₃ H

2-261 Cl

SO₂CH₃ CH₂CH₃ H

2-262 Cl

SO₂CH₃ CH₂CH₃ H

2-263 Cl

SO₂CH₃ CH₂CH₃ H

2-264 Cl

SO₂CH₃ CH₂CH₃ H

2-265 Cl

SO₂CH₃ CH₃ H

2-266 Cl

SO₂CH₃ CH₃ H

2-267 Cl

SO₂CH₃ CH₃ H

2-268 Cl

SO₂CH₃ CH₃ H

2-269 Cl

SO₂CH₃ CH₃ H

2-270 Cl

SO₂CH₃ CH₃ H

2-271 Cl

SO₂CH₃ CH₃ CH₃

2-272 Cl

SO₂CH₃ CH₃ CH₃

2-273 Cl

SO₂CH₃ CH₃ CH₃

2-274 Cl

SO₂CH₃ CH₃ CH₃

2-275 Cl

SO₂CH₃ CH₃ CH₃

2-276 Cl

SO₂CH₃ CH₃ CH₃

2-277 Cl

SO₂CH₃ CH₂CH₃ H

2-278 Cl

SO₂CH₃ CH₂CH₃ H

2-279 Cl

SO₂CH₃ CH₂CH₃ H

2-280 Cl

SO₂CH₃ CH₂CH₃ H

2-281 Cl

SO₂CH₃ CH₂CH₃ H

2-282 Cl

SO₂CH₃ CH₂CH₃ H

2-283 Cl

SO₂CH₃ CH₃ H

2-284 Cl

SO₂CH₃ CH₃ H

2-285 Cl

SO₂CH₃ CH₃ H

2-286 Cl

SO₂CH₃ CH₃ H

2-287 Cl

SO₂CH₃ CH₃ H

2-288 Cl

SO₂CH₃ CH₃ H

2-289 Cl CH₃ SO₂CH₃ CH₃ CH₃

white solid (172-174) 2-290 Cl CH₃ SO₂CH₃ CH₃ CH₃

2-291 Cl CH₃ SO₂CH₃ CH₃ CH₃

white solid (137-139) 2-292 Cl CH₃ SO₂CH₃ CH₃ CH₃

2-293 Cl CH₃ SO₂CH₃ CH₃ CH₃

2-294 Cl CH₃ SO₂CH₃ CH₃ CH₃

2-295 Cl CH₃ SO₂CH₃ CH₂CH₃ H

2-296 Cl CH₃ SO₂CH₃ CH₂CH₃ H

2-297 Cl CH₃ SO₂CH₃ CH₂CH₃ H

2-298 Cl CH₃ SO₂CH₃ CH₂CH₃ H

2-299 Cl CH₃ SO₂CH₃ CH₂CH₃ H

2-300 Cl CH₃ SO₂CH₃ CH₂CH₃ H

2-301 Cl CH₃ SO₂CH₃ CH₃ H

2-302 Cl CH₃ SO₂CH₃ CH₃ H

2-303 Cl CH₃ SO₂CH₃ CH₃ H

2-304 Cl CH₃ SO₂CH₃ CH₃ H

2-305 Cl CH₃ SO₂CH₃ CH₃ H

2-306 Cl CH₃ SO₂CH₃ CH₃ H

2-307 Cl

SO₂CH₃ CH₃ CH₃

white solid (181-183) 2-308 Cl

SO₂CH₃ CH₃ CH₃

2-309 Cl

SO₂CH₃ CH₃ CH₃

yellow solid (128-130) 2-310 Cl

SO₂CH₃ CH₃ CH₃

2-311 Cl

SO₂CH₃ CH₃ CH₃

2-312 Cl

SO₂CH₃ CH₃ CH₃

2-313 Cl

SO₂CH₃ CH₂CH₃ H

2-314 Cl

SO₂CH₃ CH₂CH₃ H

2-315 Cl

SO₂CH₃ CH₂CH₃ H

2-316 Cl

SO₂CH₃ CH₂CH₃ H

2-317 Cl

SO₂CH₃ CH₂CH₃ H

2-318 Cl

SO₂CH₃ CH₂CH₃ H

2-319 Cl

SO₂CH₃ CH₃ H

2-320 Cl

SO₂CH₃ CH₃ H

2-321 Cl

SO₂CH₃ CH₃ H

2-322 Cl

SO₂CH₃ CH₃ H

2-323 Cl

SO₂CH₃ CH₃ H

2-324 Cl

SO₂CH₃ CH₃ H

2-325 Cl

SO₂CH₃ CH₃ CH₃

2-326 Cl

SO₂CH₃ CH₃ CH₃

2-327 Cl

SO₂CH₃ CH₃ CH₃

2-328 Cl

SO₂CH₃ CH₃ CH₃

2-329 Cl

SO₂CH₃ CH₃ CH₃

2-330 Cl

SO₂CH₃ CH₃ CH₃

2-331 Cl

SO₂CH₃ CH₃ CH₃

2-332 Cl

SO₂CH₃ CH₃ CH₃

2-333 Cl

SO₂CH₃ CH₃ CH₃

2-334 Cl

SO₂CH₃ CH₃ CH₃

2-335 Cl

SO₂CH₃ CH₃ CH₃

2-336 Cl

SO₂CH₃ CH₃ CH₃

2-337 Cl

SO₂CH₃ CH₃ CH₃

2-338 Cl

SO₂CH₃ CH₃ CH₃

2-339 Cl

SO₂CH₃ CH₃ CH₃

2-340 Cl

SO₂CH₃ CH₃ CH₃

2-341 Cl

SO₂CH₃ CH₃ CH₃

2-342 Cl

SO₂CH₃ CH₃ CH₃

2-343 SO₂CH₃ H Cl CH₃ CH₃

white solid (170-171) 2-344 SO₂CH₃ H Cl CH₃ CH₃

2-345 SO₂CH₃ H Cl CH₃ CH₃

2-346 SO₂CH₃ H Cl CH₃ CH₃

2-347 SO₂CH₃ H Cl CH₃ CH₃

2-348 SO₂CH₃ H Cl CH₃ CH₃

2-349 SO₂CH₃ H Cl CH₂CH₃ H

2-350 SO₂CH₃ H Cl CH₂CH₃ H

2-351 SO₂CH₃ H Cl CH₂CH₃ H

2-352 SO₂CH₃ H Cl CH₂CH₃ H

2-353 SO₂CH₃ H Cl CH₂CH₃ H

2-354 SO₂CH₃ H Cl CH₂CH₃ H

2-355 SO₂CH₃ H Cl CH₃ H

2-356 SO₂CH₃ H Cl CH₃ H

2-357 SO₂CH₃ H Cl CH₃ H

2-358 SO₂CH₃ H Cl CH₃ H

2-359 SO₂CH₃ H Cl CH₃ H

2-360 SO₂CH₃ H Cl CH₃ H

2-361 Cl Cl SO₂CH₃ CH₃ CH₃

2-362 Cl Cl SO₂CH₃ CH₃ CH₃

2-363 Cl Cl SO₂CH₃ CH₃ CH₃

2-364 Cl Cl SO₂CH₃ CH₃ CH₃

2-365 Cl Cl SO₂CH₃ CH₃ CH₃

2-366 Cl Cl SO₂CH₃ CH₃ CH₃

2-367 Cl Cl SO₂CH₃ CH₂CH₃ H

2-368 Cl Cl SO₂CH₃ CH₂CH₃ H

2-369 Cl Cl SO₂CH₃ CH₂CH₃ H

2-370 Cl Cl SO₂CH₃ CH₂CH₃ H

2-371 Cl Cl SO₂CH₃ CH₂CH₃ H

2-372 Cl Cl SO₂CH₃ CH₂CH₃ H

2-373 Cl Cl SO₂CH₃ CH₃ H

2-374 Cl Cl SO₂CH₃ CH₃ H

2-375 Cl Cl SO₂CH₃ CH₃ H

2-376 Cl Cl SO₂CH₃ CH₃ H

2-377 Cl Cl SO₂CH₃ CH₃ H

2-378 Cl Cl SO₂CH₃ CH₃ H

2-379 SO₂CH₃ H CF₃ CH₃ CH₃

while solid (129-131) 2-380 SO₂CH₃ H CF₃ CH₃ CH₃

pale pink solid (124-126) 2-381 Cl

SO₂CH₃ CH₃ CH₃

yellow oil 2-382 Cl

SO₂CH₃ CH₃ CH₃

yellow oil 2-383 Cl H SO₂CH₃ CH₃ CH₃

yellow solid (168-170) 2-384 Cl H SO₂CH₃ CH₃ CH₃

pale yellow solid (136-138) 2-385 Cl H Cl CH₃ CH₃

pink solid (133-135) 2-386 Cl H Cl CH₃ CH₃

while solid (112-114) 2-387 NO₂ H SO₂CH₃ CH₃ CH₃

pale yellow solid (144-146) 2-388 NO₂ H SO₂CH₃ CH₃ CH₃

orange solid (150-152) 2-389 Cl H NO₂ CH₃ CH₃

yellow oil 2-390 Cl H NO₂ CH₃ CH₃

yellow solid (115-117) 2-391 NO₂ H Cl CH₃ CH₃

pale yellow solid (128-130) 2-392 NO₂ H Cl CH₃ CH₃

pale yellow solid (134-136) 2-393 Cl

SO₂CH₃ CH₃ CH₃

2-394 Cl

SO₂CH₃ CH₃ CH₃

2-395 Cl

SO₂CH₃ CH₃ CH₃

2-396 Cl

SO₂CH₃ CH₃ CH₃

2-397 Cl

SO₂CH₃ CH₃ CH₃

2-398 Cl

SO₂CH₃ CH₃ CH₃

2-399 Cl

SO₂CH₃ CH₂CH₃ H

2-400 Cl

SO₂CH₃ CH₂CH₃ H

2-401 Cl

SO₂CH₃ CH₂CH₃ H

2-402 Cl

SO₂CH₃ CH₂CH₃ H

2-403 Cl

SO₂CH₃ CH₂CH₃ H

2-404 Cl

SO₂CH₃ CH₂CH₃ H

2-405 Cl

SO₂CH₃ CH₃ H

2-406 Cl

SO₂CH₃ CH₃ H

2-407 Cl

SO₂CH₃ CH₃ H

2-408 Cl

SO₂CH₃ CH₃ H

2-409 Cl

SO₂CH₃ CH₃ H

2-410 Cl

SO₂CH₃ CH₃ H

2-411 Cl CH₃SO₂CH₂ SO₂CH₃ CH₃ CH₃

2-412 Cl CH₃SO₂CH₂ SO₂CH₃ CH₂CH₃ H

2-413 Cl CH₃SO₂CH₂ SO₂CH₃ CH₃ H

2-414 CH₃

SO₂CH₃ CH₃ CH₃

yellow solid (147-149) 2-415 CH₃

SO₂CH₃ CH₃ CH₃

yellow solid (167-169) 2-416 CH₃

SO₂CH₃ CH₃

yellow oil 2-417 CH₃

SO₂CH₃ CH₃

yellow solid (110-111) 2-418 CH₃

SO₂CH₃ CH₃

yellow solid (101-103) 2-419 CH₃

SO₂CH₃ CH₃

yellow oil 2-420 CH₃

SO₂CH₃ CH₂CH₃ CH₃

yellow solid (105-106) 2-421 Cl

SO₂CH₃ CH₃ CH₃

pink oil

In the compound of the formula I, W is N and the stereo configuration is trans.

TABLE 3 Structures and Physical Properties of Part of Compounds of Formula I Appear- ance (Melting Com- Point pound X₁ X₃ Z₁ Z₂ R₁ R₂ R₃ R₄ R₅ ° C.) 3-1 SO₂CH₃ CF₃ CH₃ CH₃ H H H H H 3-2 SO₂CH₃ CF₃

CH₃ H H H H H 3-3 SO₂CH₃ CF₃ CH₃

H H H H H 3-4 SO₂CH₃ CF₃ CH₃ CH₃ Cl H Cl H H 3-5 SO₂CH₃ CF₃

CH₃ Cl H Cl H H 3-6 SO₂CH₃ CF₃ CH₃

Cl H Cl H H 3-7 SO₂CH₃ CF₃ CH₃ CH₃ H H OCH₃ H H 3-8 SO₂CH₃ CF₃

CH₃ H H OCH₃ H H 3-9 SO₂CH₃ CF₃ CH₃

H H OCH₃ H H 3-10 SO₂CH₃ CF₃ CH₃ CH₃ H H NO₂ H H 3-11 SO₂CH₃ CF₃

CH₃ H H NO₂ H H 3-12 SO₂CH₃ CF₃ CH₃

H H NO₂ H H 3-13 SO₂CH₃ CF₃ CH₃ CH₃ H H CF₃ H H 3-14 SO₂CH₃ CF₃

CH₃ H H CF₃ H H 3-15 SO₂CH₃ CF₃ CH₃

H H CF₃ H H 3-16 SO₂CH₃ CF₃ CH₃ CH₃ H OCF₃ H H H 3-17 SO₂CH₃ CF₃

CH₃ H OCF₃ H H H 3-18 SO₂CH₃ CF₃ CH₃

H OCF₃ H H H 3-19 SO₂CH₃ CF₃ CH₃ CH₃ H H

H H 3-20 SO₂CH₃ CF₃

CH₃ H H

H H 3-21 SO₂CH₃ CF₃ CH₃

H H

H H 3-22 SO₂CH₃ CF₃ CH₃ CH₃ H

H H 3-23 SO₂CH₃ CF₃

CH₃ H

H H 3-24 SO₂CH₃ CF₃ CH₃

H

H H 3-25 SO₂CH₃ CF₃ CH₃ CH₃ H

H H 3-26 SO₂CH₃ CF₃

CH₃ H

H H 3-27 SO₂CH₃ CF₃ CH₃

H

H H 3-28 SO₂CH₃ CF₃ CH₃ CH₃ H

H H 3-29 SO₂CH₃ CF₃

CH₃ H

H H 3-30 SO₂CH₃ CF₃ CH₃

H

H H 3-31 SO₂CH₃ CF₃ CH₃ CH₃

H H H 3-32 SO₂CH₃ CF₃

CH₃

H H H 3-33 SO₂CH₃ CF₃ CH₃

H H H 3-34 NO₂ SO₂CH₃ CH₃ CH₃ H H H H H 3-35 NO₂ SO₂CH₃

CH₃ H H H H H 3-36 NO₂ SO₂CH₃ CH₃

H H H H H 3-37 NO₂ SO₂CH₃ CH₃ CH₃ H

H H 3-38 NO₂ SO₂CH₃

CH₃ H

H H 3-39 NO₂ SO₂CH₃ CH₃

H

H H 3-40 NO₂ Cl CH₃ CH₃ H H H H H 3-41 NO₂ Cl

CH₃ H H H H H 3-42 NO₂ Cl CH₃

H H H H H 3-43 Cl Cl CH₃ CH₃ H H H H H 3-44 Cl Cl

CH₃ H H H H H 3-45 Cl Cl CH₃

H H H H H 3-46 Cl Cl CH₃ CH₃ H

H H 3-47 Cl Cl

CH₃ H

H H 3-48 Cl Cl CH₃

H

H H 3-49 Cl SO₂CH₃ CH₃ CH₃ H H H H H 3-50 Cl SO₂CH₃

CH₃ H H H H H 3-51 Cl SO₂CH₃ CH₃

H H H H H 3-52 Cl SO₂CH₃ CH₃ CH₃ H

H H 3-53 Cl SO₂CH₃

CH₃ H

H H 3-54 Cl SO₂CH₃ CH₃

H

H H 3-55 CH₃ CH₃ CH₃ H H H H H 3-56 CH₃ SO₂CH₃

CH₃ H H H H H 3-57 CH₃ SO₂CH₃ CH₃

H H H H H 3-58 CN SO₂CH₃ CH₃ CH₃ H H H H H 3-59 CN SO₂CH₃

CH₃ H H H H H 3-60 CN SO₂CH₃ CH₃

H H H H H 3-61 CF₃ SO₂CH₃ CH₃ CH₃ H H H H H 3-62 CF₃ SO₂CH₃

CH₃ H H H H H 3-63 CF₃ SO₂CH₃ CH₃

H H H H H 3-64

SO₂CH₃ CH₃ CH₃ H H H H H 3-65

SO₂CH₃

CH₃ H H H H H 3-66

SO₂CH₃ CH₃

H H H H H 3-67

SO₂CH₃ CH₃ CH₃ H H H H H 3-68

SO₂CH₃

CH₃ H H H H H 3-69

SO₂CH₃ CH₃

H H H H H 3-70

SO₂CH₃ CH₃ CH₃ H H H H H 3-71

SO₂CH₃

CH₃ H H H H H 3-72

SO₂CH₃ CH₃

H H H H H 3-73

SO₂CH₃ CH₃ CH₃ H H H H H 3-74

SO₂CH₃

CH₃ H H H H H 3-75

SO₂CH₃ CH₃

H H H H H 3-76

SO₂CH₃ CH₃ CH₃ H H H H H 3-77

SO₂CH₃

CH₃ H H H H H 3-78

SO₂CH₃ CH₃

H H H H H 3-79

SO₂CH₃ CH₃ CH₃ H H H H H 3-80

SO₂CH₃

CH₃ H H H H H 3-81

SO₂CH₃ CH₃

H H H H H 3-82

SO₂CH₃ CH₃ CH₃ H H H H H 3-83

SO₂CH₃

CH₃ H H H H H 3-84

SO₂CH₃ CH₃

H H H H H 3-85 SO2CH═CH₂ SO₂CH₃ CH₃ CH₃ H H H H H 3-86 SO2CH═CH₂ SO₂CH₃

CH₃ H H H H H 3-87 SO2CH═CH₂ SO₂CH₃ CH₃

H H H H H 3-88

SO₂CH₃ CH₃ CH₃ H H H H H 3-89

SO₂CH₃

CH₃ H H H H H 3-90

SO₂CH CH₃

H H H H H 3-91

SO₂CH₃ CH₃ CH₃ H H H H H 3-92

SO₂CH₃

CH₃ H H H H H 3-93

SO₂CH₃ CH₃

H H H H H 3-94

SO₂CH₃ CH₃ CH₃ H H H H H 3-95

SO₂CH₃

CH₃ H H H H H 3-96

SO₂CH CH₃

H H H H H 3-97

SO₂CH₃ CH₃ CH₃ H H H H H 3-98

SO₂CH₃

CH₃ H H H H H 3-99

SO₂CH₃ CH₃

H H H H H 3-100

SO₂CH₃ CH₃ CH₃ H H H H H 3-101

SO₂CH₃

CH₃ H H H H H 3-102

SO₂CH₃ CH₃

H H H H H 3-103

SO₂CH₃ CH₃ CH₃ H H H H H 3-104

SO₂CH₃

CH₃ H H H H H 3-105

SO₂CH₃ CH₃

H H H H H 3-106

SO₂CH₃ CH₃ CH₃ H H H H H 3-107

SO₂CH₃

CH₃ H H H H H 3-108

SO₂CH₃ CH₃

H H H H H 3-109 H Cl CH₃ CH₃ H H H H H white solid (115- 120)

In the compound of the formula I, W is N.

TABLE 4 Structures and Physical Properties of Part of Compounds of Formula I Appearance (Melting Compound X₁ X₃ R₁ R₂ Z Point ° C.) 4-1  SO₂CH₃ CF₃ CH₃ CH₃

4-2  SO₂CH₃ CF₃

CH₃

4-3  SO₂CH₃ CF₃ CH₃

4-4  SO₂CH₃ CF₃ CH₃ CH₃

4-5  SO₂CH₃ CF₃

CH₃

4-6  SO₂CH₃ CF₃ CH₃

4-7  SO₂CH₃ CF₃ CH₃ CH₃

4-8  SO₂CH₃ CF₃

CH₃

4-9  SO₂CH₃ CF₃ CH₃

4-10  SO₂CH₃ CF₃ CH₃ CH₃

4-11  SO₂CH₃ CF₃

CH₃

4-12  SO₂CH₃ CF₃ CH₃

4-13  SO₂CH₃ CF₃ CH₃ CH₃

4-14  SO₂CH₃ CF₃

CH₃

4-15  SO₂CH₃ CF₃ CH₃

4-16  SO₂CH₃ CF₃ CH₃ CH₃

4-17  SO₂CH₃ CF₃

CH₃

4-18  SO₂CH₃ CF₃ CH₃

4-19  SO₂CH₃ CF₃ CH₃ CH₃

4-20  SO₂CH₃ CF₃

CH₃

4-21  SO₂CH₃ CF₃ CH₃

4-22  SO₂CH₃ CF₃ CH₃ CH₃

4-23  SO₂CH₃ CF₃

CH₃

4-24  SO₂CH₃ CF₃ CH₃

4-25  SO₂CH₃ CF₃ CH₃ CH₃

4-26  SO₂CH₃ CF₃

CH₃

4-27  SO₂CH₃ CF₃ CH₃

4-28  SO₂CH₃ CF₃ CH₃ CH₃

4-29  SO₂CH₃ CF₃

CH₃

4-30  SO₂CH₃ CF₃ CH₃

4-31  SO₂CH₃ CF₃ CH₃ CH₃

4-32  SO₂CH₃ CF₃

CH₃

4-33  SO₂CH₃ CF₃ CH₃

4-34  NO₂ SO₂CH₃ CH₃ CH₃

4-35  NO₂ SO₂CH₃

CH₃

4-36  NO₂ SO₂CH₃ CH₃

4-37  NO₂ SO₂CH₃ CH₃ CH₃

4-38  NO₂ SO₂CH₃

CH₃

4-39  NO₂ SO₂CH₃ CH₃

4-40  NO₂ Cl CH₃ CH₃

4-41  NO₂ Cl

CH₃

4-42  NO₂ Cl CH₃

4-43  Cl Cl CH₃ CH₃

4-44  Cl Cl

CH₃

4-45  Cl Cl CH₃

4-46  Cl Cl CH₃ CH₃

4-47  Cl Cl

CH₃

4-48  Cl Cl CH₃

4-49  Cl SO₂CH₃ CH₃ CH₃

4-50  Cl SO₂CH₃

CH₃

4-51  Cl SO₂CH₃ CH₃

4-52  Cl SO₂CH₃ CH₃ CH₃

4-53  Cl SO₂CH₃

CH₃

4-54  Cl SO₂CH₃ CH₃

4-55  CH₃ SO₂CH₃ CH₃ CH₃

4-56  CH₃ SO₂CH₃

CH₃

4-57  CH₃ SO₂CH₃ CH₃

4-58  CN SO₂CH₃ CH₃ CH₃

4-59  CN SO₂CH₃

CH₃

4-60  CN SO₂CH₃ CH₃

4-61  CF₃ SO₂CH₃ CH₃ CH₃

4-62  CF₃ SO₂CH₃

CH₃

4-63  CF₃ SO₂CH₃ CH₃

4-64 

SO₂CH₃ CH₃ CH₃

4-65 

SO₂CH₃

CH₃

4-66 

SO₂CH₃ CH₃

4-67 

SO₂CH₃ CH₃ CH₃

4-68 

SO₂CH₃

CH₃

4-69 

SO₂CH₃ CH₃

4-70 

SO₂CH₃ CH₃ CH₃

4-71 

SO₂CH₃

CH₃

4-72 

SO₂CH₃ CH₃

4-73 

SO₂CH₃ CH₃ CH₃

4-74 

SO₂CH₃

CH₃

4-75 

SO₂CH₃ CH₃

4-76 

SO₂CH₃ CH₃ CH₃

4-77 

SO₂CH₃

CH₃

4-78 

SO₂CH₃ CH₃

4-79 

SO₂CH₃ CH₃ CH₃

4-80 

SO₂CH₃

CH₃

4-81 

SO₂CH₃ CH₃

4-82 

SO₂CH₃ CH₃ CH₃

4-83 

SO₂CH₃

CH₃

4-84 

SO₂CH₃ CH₃

4-85  SO₂CH═CH₂ SO₂CH₃ CH₃ CH₃

4-86  SO₂CH═CH₂ SO₂CH₃

CH₃

4-87  SO₂CH═CH₂ SO₂CH₃ CH₃

4-88 

SO₂CH₃ CH₃ CH₃

4-89 

SO₂CH₃

CH₃

4-90 

SO₂CH₃ CH₃

4-91 

SO₂CH₃ CH₃ CH₃

4-92 

SO₂CH₃

CH₃

4-93 

SO₂CH₃ CH₃

4-94 

SO₂CH₃ CH₃ CH₃

4-95 

SO₂CH₃

CH₃

4-96 

SO₂CH₃ CH₃

4-97 

SO₂CH₃ CH₃ CH₃

4-98 

SO₂CH₃

CH₃

4-99 

SO₂CH₃ CH₃

4-100

SO₂CH₃ CH₃ CH₃

4-101

SO₂CH₃

CH₃

4-102

SO₂CH₃ CH₃

4-103

SO₂CH₃ CH₃ CH₃

4-104

SO₂CH₃

CH₃

4-105

SO₂CH₃ CH₃

4-106

SO₂CH₃ CH₃ CH₃

4-107

SO₂CH₃

CH₃

4-108

SO₂CH₃ CH₃

4-109

CF₃ CH₃ CH₃

4-110

CF₃ CH₃ CH₃

4-111

CF₃ CH₃ CH₃

4-112

CF₃ CH₃ CH₃

4-113

CF₃ CH₃ CH₃

4-114

CF₃ CH₃ CH₃

4-115

CF₃ CH₃ CH₃

4-116

CF₃ CH₃ CH₃

4-117

CF₃ CH₃ CH₃

4-118

CF₃ CH₃ CH₃

4-119

CF₃ CH₃ CH₃

4-120

CF₃ CH₃ CH₃

4-121

CF₃ CH₃ CH₃

4-122

CF₃ CH₃ CH₃

4-123

CF₃ CH₃ CH₃

4-124

CF₃ CH₃ CH₃

4-125

CF₃ CH₃ CH₃

4-126

CF₃ CH₃ CH₃

4-127

CF₃ CH₃ CH₃

4-128

CF₃ CH₃ CH₃

4-129

CF₃ CH₃ CH₃

4-130

CF₃ CH₃ CH₃

4-131

CF₃ CH₃ CH₃

4-132

CF₃ CH₃ CH₃

4-133

CF₃ CH₃ CH₃

4-134

CF₃ CH₃ CH₃

4-135

CF₃ CH₃ CH₃

4-136

CF₃ CH₃ CH₃

4-137

CF₃ CH₃ CH₃

4-138

CF₃ CH₃ CH₃

4-139

CF₃ CH₃ CH₃

4-140 H Cl CH₃ CH₃

white solid (122-126) 4-141 H Cl CH₃ CH₃

yellow solid (105-109) ¹H NMR data of part of compounds is as follows:

Compound 1-1 (600 MHz, DMSO-d₆): 8.11 (s, 2H), 7.63-7.67 (m, 3H), 7.42-7.51 (m, 4H), 6.28 (d, 1H), 3.57 (s, 3H), 3.34 (s, 3H), 2.33 (s, 3H).

Compound 1-7 (600 MHz, CDCl₃): 8.18 (s, 1H), 7.81 (d, 1H), 7.45 (d, 1H), 7.37 (d, 1H), 6.96 (dd, 1H), 6.90 (s, 1H), 6.82 (d, 1H), 6.03 (s, 2H), 5.76 (d, 1H), 3.57 (s, 3H), 3.26 (s, 3H), 2.42 (s, 3H).

Compound 1-16 (600 MHz, CDCl₃): 8.03 (d, 1H), 7.59 (d, 1H), 7.37-7.48 (m, 6H), 6.09 (d, 1H), 4.98 (s, 2H), 3.61 (s, 3H), 3.47 (s, 3H), 2.81 (s, 3H), 2.47 (s, 3H).

Compound 1-18 (600 MHz, DMSO-d₆): 7.98 (d, 1H), 7.56-7.65 (m, 4H), 6.98 (d, 2H), 6.15 (d, 1H), 4.86 (s, 2H), 3.82 (s, 3H), 3.57 (s, 3H), 3.34 (s, 3H), 2.94 (s, 3H), 2.35 (s, 3H).

Compound 1-20 (600 MHz, DMSO-d₆): 7.98 (d, 1H), 7.90 (d, 2H), 7.78 (d, 2H), 7.70 (d, 1H), 7.60 (d, 1H), 6.50 (d, 1H), 4.84 (s, 2H), 3.60 (s, 3H), 3.32 (s, 3H), 3.01 (s, 3H), 2.34 (s, 3H).

Compound 1-21 (600 MHz, DMSO-d₆): 8.00 (d, 1H), 7.74-7.79 (m, 6H), 7.68 (d, 1H), 7.61 (d, 1H), 7.50 (t, 2H), 7.42 (t, 1H), 6.38 (d, 1H), 4.86 (s, 2H), 3.60 (s, 3H), 3.34 (s, 3H), 2.97 (s, 3H), 2.34 (s, 3H).

Compound 1-22 (600 MHz, DMSO-d₆): 7.98 (d, 1H), 7.58 (d, 1H), 7.52 (d, 1H), 7.33 (s, 1H), 7.19 (d, 1H), 6.97 (d, 1H), 6.18 (d, 1H), 6.11 (s, 2H), 4.86 (s, 2H), 3.57 (s, 3H), 3.35 (s, 3H), 2.99 (s, 3H), 2.34 (s, 3H).

Compound 1-31 (600 MHz, CDCl₃): 8.01 (d, 1H), 7.63 (d, 1H), 7.44-7.49 (m, 5H), 7.28 (d, 1H), 6.03 (d, 1H), 3.62 (s, 3H), 2.84 (s, 3H), 2.67 (s, 3H), 2.45 (s, 3H).

Compound 1-37 (600 MHz, DMSO-d₆): 7.92 (d, 1H), 7.55 (d, 1H), 7.42 (d, 11H), 7.37 (s, 1H), 7.22 (d, 1H), 6.98 (d, 1H), 6.21 (d, 1H), 6.11 (s, 2H), 3.56 (s, 3H), 2.99 (s, 3H), 2.59 (s, 3H), 2.33 (s, 3H).

Compound 1-42 (600 MHz, CDCl₃): 8.05 (d, 1H), 7.71 (t, 2H), 7.35 (d, 1H), 7.06 (s, 1H), 7.05 (s, 1H), 6.86 (d, 1H), 6.18 (d, 1H), 6.06 (s, 2H), 3.74 (s, 3H), 3.03 (s, 3H), 2.76 (s, 3H).

Compound 1-76 (600 MHz, DMSO-d₆): 7.99 (d, 1H), 7.60-7.70 (m, 4H), 7.43-7.51 (m, 3H), 6.34 (d, 1H), 4.95 (s, 2H), 3.65 (t, 2H), 3.60 (s, 3H), 3.47 (t, 2H), 3.23 (s, 3H), 2.99 (s, 3H), 2.34 (s, 3H).

Compound 1-81 (600 MHz, CDCl₃): 8.07 (d, 1H), 7.65-7.67 (m, 3H), 7.62 (d, 2H), 7.58 (d, 2H), 7.46-7.48 (m, 2H), 7.39-7.41 (m, 2H), 6.10 (d, J=15.6 Hz, 1H), 5.10 (s, 2H), 3.76-3.78 (m, 2H), 3.62 (s, 3H), 3.58-3.59 (m, 2H), 3.34 (s, 3H), 2.99 (s, 3H), 2.46 (s, 3H).

Compound 1-82 (600 MHz, CDCl₃): 8.04 (d, 1H), 7.48 (d, 1H), 7.37 (d, 1H), 6.99-7.00 (m, 2H), 6.83 (d, 1H), 6.04 (s, 2H), 5.86 (d, 1H), 5.10 (s, 2H), 3.76-3.78 (m, 2H), 3.60 (s, 3H), 3.58-3.59 (m, 2H), 3.35 (s, 3H), 3.03 (s, 3H), 2.46 (s, 3H).

Compound 1-115 (600 MHz, CDCl₃): 7.85 (d, 1H), 7.62 (d, 1H), 7.40-7.50 (m, 5H), 7.18 (d, 1H), 6.09 (d, 1H), 4.00 (s, 3H), 3.62 (s, 3H), 2.83 (s, 3H), 2.44 (s, 3H).

Compound 1-223 (600 MHz, DMSO-d₆): 7.97 (d, 2H), 7.65-7.71 (m, 4H), 7.44-7.48 (m, 31H), 6.40 (d, 1H), 3.60 (s, 3H), 2.93 (s, 3H), 2.32 (s, 3H).

Compound 1-226 (600 MHz, DMSO-d₆): 8.01 (s, 1H), 7.90 (d, 1H), 7.62 (d, 1H), 7.55 (d, 1H), 7.37 (s, 1H), 7.21 (d, 1H), 6.97 (d, 1H), 6.24 (d, 1H), 6.11 (s, 2H), 3.58 (s, 3H), 2.99 (s, 3H), 2.33 (s, 3H).

Compound 1-229 (600 MHz, DMSO-d₆): 7.73 (d, 2H), 7.60 (d, 1H), 7.56 (d, 1H), 7.46-7.52 (m, 3H), 7.43 (dd, 1H), 7.36 (d, 1H), 6.39 (d, 1H), 3.59 (s, 3H), 2.33 (s, 3H).

Compound 1-232 (600 MHz, DMSO-d₆): 7.59 (s, 1H), 7.46 (d, 1H), 7.40-7.43 (m, 2H), 7.34 (d, 1H), 7.22 (d, 1H), 7.00 (d, 1H), 6.23 (d, 1H), 6.12 (s, 2H), 3.57 (s, 3H), 2.32 (s, 3H).

Compound 1-235 (600 MHz, DMSO-d₆): 8.58 (s, 1H), 8.36 (d, 1H), 7.84 (d, 1H), 7.69 (d, 2H), 7.62 (d, 1H), 7.44-7.51 (m, 3H), 6.37 (d, 1H), 3.58 (s, 3H), 3.01 (s, 3H), 2.35 (s, 3H).

Compound 1-238 (600 MHz, DMSO-d₆): 8.58 (s, 1H), 8.34 (d, 1H), 7.82 (d, 1H), 7.51 (d, 1H), 7.36 (s, 1H), 7.20 (d, 1H), 6.98 (d, 1H), 6.20 (d, 1H), 6.12 (s, 2H), 3.55 (s, 3H), 3.07 (s, 3H), 2.36 (s, 3H).

Compound 1-259 (600 MHz, DMSO-d₆): 7.68-7.70 (m, 3H), 7.62 (d, 1H), 7.48 (t, 1H), 7.42-7.44 (m, 2H), 7.23 (d, 1H), 6.40 (d, 1H), 4.01 (t, 2H), 3.62 (t, 2H), 3.59 (s, 3H), 3.30 (s, 3H), 2.88 (s, 3H), 2.34 (s, 3H), 2.17 (s, 3H).

Compound 1-262 (600 MHz, CDCl₃): 7.78 (d, 1H), 7.44 (d, 1H), 7.13 (d, 1H), 6.93-6.96 (m, 2H), 6.81 (d, 1H), 6.01 (s, 2H), 5.83 (d, 1H), 4.09 (t, 2H), 3.69 (t, 2H), 3.58 (s, 3H), 3.40 (s, 3H), 2.96 (s, 3H), 2.39 (s, 3H), 2.26 (s, 3H).

Compound 1-265 (600 MHz, CDCl₃): 7.82 (d, 1H), 7.58 (d, 1H), 7.41-7.49 (m, 5H), 7.17 (d, 1H), 6.07 (d, 1H), 3.85 (s, 3H), 3.63 (s, 3H), 2.84 (s, 3H), 2.44 (s, 3H), 2.28 (s, 3H).

Compound 1-268 (600 MHz, CDCl₃): 7.95 (d, 1H), 7.59 (d, 1H), 7.41-7.48 (m, 5H), 7.22 (d, 1H), 5.98 (d, 1H), 3.61 (s, 3H), 2.81 (s, 3H), 2.52 (s, 3H), 2.42 (s, 3H), 2.23 (s, 3H).

Compound 1-280 (600 MHz, CDCl₃): 7.78 (d, 1H), 7.55 (d, 1H), 7.39-7.47 (m, 5H), 7.12 (d, 1H), 6.04 (d, 1H), 3.97 (q, 2H), 3.61 (s, 3H), 2.83 (s, 3H), 2.42 (s, 3H), 2.24 (s, 3H), 1.37 (t, 3H).

Compound 1-292 (600 MHz, CDCl₃): 8.00 (d, 1H), 7.79 (d, 1H), 7.75 (s, 1H), 7.53-7.56 (m, 3H), 7.41-7.47 (m, 3H), 6.40 (d, 1H), 4.54 (t, 2H), 3.75 (s, 3H), 3.29 (brs, 2H), 2.92 (s, 3H), 2.28 (s, 3H).

Compound 1-346 (600 MHz, CDCl₃): 7.85 (d, 1H), 7.57 (d, 1H), 7.43-7.50 (m, 5H), 7.27 (d, 1H), 6.05 (d, 1H), 4.34 (q, 2H), 3.63 (s, 3H), 2.80 (s, 3H), 2.47 (s, 3H), 2.31 (s, 3H).

Compound 1-349 (600 MHz, CDCl₃): 7.83 (d, 1H), 7.58 (d, 1H), 7.41-7.49 (m, 5H), 7.17 (d, 1H), 6.05 (d, 1H), 4.27-4.31 (m, 1H), 3.81-3.39 (m, 4H), 3.63 (s, 3H), 2.91 (s, 3H), 2.44 (s, 3H), 2.30 (s, 3H), 1.94-1.99 (m, 1H), 1.84-1.91 (m, 2H), 1.49-1.55 (m, 1H).

Compound 1-367 (600 MHz, CDCl₃): 8.04 (s, 1H), 7.46-7.60 (m, 7H), 7.33 (d, 1H), 6.06 (d, 1H), 3.58 (s, 3H), 2.47 (s, 3H).

Compound 1-370 (600 MHz, CDCl₃): 7.82 (d, 1H), 7.52 (d, 1H), 7.43 (d, 2H), 7.17 (d, 1H), 6.92 (d, 2H), 5.88 (d, 1H), 4.10 (t, 2H), 3.86 (s, 3H), 3.69 (t, 2H), 3.61 (s, 3H), 3.42 (s, 3H), 2.91 (s, 3H), 2.44 (s, 3H), 2.29 (s, 3H).

Compound 1-371 (600 MHz, CDCl₃): 7.93 (d, 1H), 7.50-7.56 (m, 4H), 7.42-7.49 (m, 3H), 7.29 (d, 1H), 6.10 (d, 1H), 3.61 (s, 3H), 3.26 (s, 3H), 2.40 (s, 3H).

Compound 1-372 (600 MHz, CDCl₃): 7.86 (d, 1H), 7.81 (d, 1H), 7.70 (s, 1H), 7.55-7.57 (m, 2H), 7.41-7.46 (m, 3H), 7.26 (d, 1H), 6.44 (d, 1H), 4.17 (t, 2H), 4.03-4.07 (m, 2H), 3.75 (t, 2H), 3.44 (s, 3H), 3.10 (s, 3H), 2.33 (s, 3H), 1.46 (t, 3H).

Compound 1-373 (600 MHz, CDCl₃): 7.87 (d, 1H), 7.65 (d, 1H), 7.41-7.51 (m, 5H), 7.19 (d, 1H), 6.11 (d, 1H), 4.32 (t, 2H), 3.79 (t, 2H), 3.62 (s, 3H), 3.57 (q, 2H), 2.89 (s, 3H), 2.43 (s, 3H), 1.22 (t, 3H).

Compound 1-374 (600 MHz, CDCl₃): 7.87 (d, 1H), 7.64 (d, 1H), 7.41-7.51 (m, 5H), 7.18 (d, 1H), 6.10 (d, 1H), 4.24 (t, 2H), 3.62 (s, 3H), 3.55 (t, 2H), 3.34 (s, 3H), 2.87 (s, 3H), 2.44 (s, 3H), 2.09-2.10 (m, 2H).

Compound 1-375 (600 MHz, CDCl₃): 7.84 (d, 1H), 7.59 (d, 1H), 7.39-7.49 (m, 5H), 7.15 (d, 1H), 6.07 (d, 1H), 4.15 (t, 2H), 3.60 (s, 3H), 3.41 (t, 2H), 3.32 (s, 3H), 2.82 (s, 3H), 2.43 (s, 3H), 1.88-1.89 (m, 2H), 1.69-1.70 (m, 2H).

Compound 1-376 (600 MHz, CDCl₃): 7.85 (d, 1H), 7.62 (d, 1H), 7.40-7.50 (m, 5H), 7.15 (d, 1H), 6.08 (d, 1H), 4.10 (td, 2H), 3.61 (s, 3H), 2.84 (s, 3H), 2.44 (s, 3H), 1.84 (p, 2H), 0.99 (t, 3H).

Compound 1-377 (600 MHz, CDCl₃): 7.89 (d, 1H), 7.66 (d, 1H), 7.40-7.51 (m, 5H), 7.11 (d, 1H), 6.12 (d, 1H), 5.21-5.27 (m, 1H), 3.62 (s, 3H), 2.83 (s, 3H), 2.40 (s, 3H), 1.35 (d, 6H).

Compound 2-1 (600 MHz, CDCl₃): 7.79 (d, 1H), 7.11 (d, 1H), 6.82-6.84 (m, 1H), 3.91 (s, 3H), 3.57 (s, 3H), 3.21 (s, 3H), 2.47 (s, 3H), 2.23 (s, 3H), 2.21 (q, 2H), 2.00-2.02 (m, 2H), 1.57-1.64 (m, 4H).

Compound 2-19 (600 MHz, CDCl₃): 7.80 (d, 1H), 7.10 (d, 1H), 6.81-6.83 (m, 1H), 4.07 (q, 2H), 3.56 (s, 3H), 3.22 (s, 3H), 2.47 (s, 3H), 2.21 (s, 3H), 2.19-2.22 (m, 2H), 1.99-2.02 (m, 2H), 1.58-1.63 (m, 4H), 1.48 (t, 3H).

Compound 2-37 (600 MHz, CDCl₃): 7.84 (d, 1H), 7.22 (d, 1H), 6.85-6.87 (m, 1H), 4.46 (q, 2H), 3.57 (s, 3H), 3.24 (s, 3H), 2.46 (s, 3H), 2.25 (s, 3H), 2.20 (q, 2H), 1.98-2.01 (m, 2H), 1.57-1.64 (m, 4H).

Compound 2-55 (600 MHz, CDCl₃): 7.80 (d, 1H), 7.12 (d, 1H), 6.85 (t, 1H), 4.18 (t, 2H), 3.80 (t, 2H), 3.57 (s, 3H), 3.47 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.26 (s, 3H), 2.19-2.21 (m, 2H), 2.00-2.01 (m, 2H), 1.57-1.63 (m, 4H).

Compound 2-57 (600 MHz, CDCl₃): 7.78 (d, 1H), 7.09 (d, 1H), 6.68 (t, 1H), 4.15 (t, 2H), 3.78 (t, 2H), 3.56 (s, 3H), 3.45 (s, 3H), 3.24 (s, 3H), 2.50-2.52 (m, 2H), 2.43 (s, 3H), 2.32-2.34 (m, 2H), 2.24 (s, 3H), 1.93-1.95 (m, 2H).

Compound 2-61 (600 MHz, CDCl₃): 7.84 (d, 1H), 7.72 (s, 1H), 7.22 (d, 1H), 7.12-7.13 (m, 1H), 4.21 (t, 2H), 3.97-4.00 (m, 2H), 3.79 (t, 2H), 3.46 (s, 3H), 3.27 (s, 3H), 2.30 (s, 3H), 2.20-2.21 (m, 2H), 2.19-2.20 (m, 2H), 1.65-1.70 (m, 2H), 1.62-1.64 (m, 2H), 1.43 (t, 3H).

Compound 2-63 (600 MHz, CDCl₃): 7.82-7.84 (m, 1H), 7.72 (s, 1H), 7.22 (d, 1H), 6.70 (d, 1H), 4.20 (d, 2H), 3.97-4.01 (m, 2H), 3.79 (d, 2H), 3.45 (s, 3H), 3.27 (s, 3H), 2.53-2.60 (m, 4H), 2.32 (s, 3H), 2.00-2.03 (m, 2H), 1.42 (t, 3H).

Compound 2-67 (600 MHz, CDCl₃): 7.85 (d, 1H), 7.73 (s, 1H), 7.22 (d, 1H), 7.12-7.13 (m, 1H), 4.20 (t, 2H), 3.80 (t, 2H), 3.70 (s, 3H), 3.47 (s, 3H), 3.28 (s, 3H), 2.31 (s, 3H), 2.25-2.28 (m, 2H), 2.20-2.22 (m, 2H), 1.67-1.70 (m, 2H), 1.62-1.65 (m, 2H).

Compound 2-73 (600 MHz, CDCb3): 7.81 (d, 1H), 7.11 (d, 1H), 6.82-6.84 (m, 1H), 4.35-4.39 (m, 1H), 4.01 (d, 2H), 3.85-3.97 (m, 2H), 3.56 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.26 (s, 3H), 2.19-2.20 (m, 2H), 1.95-2.00 (m, 4H), 1.57-1.63 (m, 6H).

Compound 2-121 (600 MHz, CDCl₃): 8.01 (d, 1H), 7.75 (s, 1H), 7.50 (d, 1H), 7.10-7.12 (m, 1H), 4.57 (t, 2H), 3.69 (s, 3H), 3.36-3.32 (m, 2H), 3.18 (s, 3H), 2.25-2.28 (m, 5H), 2.09-2.10 (m, 2H), 1.67-1.69 (m, 2H), 1.62-1.63 (m, 2H).

Compound 2-123 (600 MHz, CDCl₃): 8.01 (d, 1H), 7.76 (s, 1H), 7.51 (d, 1H), 6.95-6.98 (m, 1H), 4.58 (t, 2H), 3.71 (s, 3H), 3.32-3.37 (m, 2H), 3.19 (s, 3H), 2.58-2.62 (m, 2H), 2.52-2.54 (m, 2H), 2.26 (s, 3H), 2.01-2.04 (m, 2H).

Compound 2-127 (600 MHz, CDCl₃): 7.92 (d, 1H), 7.15 (d, 1H), 6.68-6.69 (m, 1H), 3.55 (s, 3H), 3.05 (s, 3H), 2.61 (s, 3H), 2.49 (s, 3H), 2.19 (s, 3H), 2.16-2.17 (m, 2H), 1.94-1.95 (m, 2H), 1.55-1.65 (m, 4H).

Compound 2-145 (600 MHz, CDCl₃): 7.95 (d, 1H), 7.26 (d, 1H), 6.69-6.70 (m, 1H), 4.87 (s, 2H), 3.54 (s, 3H), 3.47 (s, 3H), 3.15 (s, 3H), 2.47 (s, 3H), 2.31 (s, 3H), 2.15-2.16 (m, 2H), 1.94-1.95 (m, 2H), 1.56-1.60 (m, 4H).

Compound 2-289 (600 MHz, CDCl₃): 7.98 (d, 1H), 7.20 (d, 1H), 6.72 (s, 1H), 3.54 (s, 3H), 3.07 (s, 3H), 2.74 (s, 3H), 2.49 (s, 3H), 2.16-2.17 (m, 2H), 1.96-1.97 (m, 2H), 1.55-1.60 (m, 4H).

Compound 2-291 (600 MHz, CDCl₃): 7.97 (d, 1H), 7.21 (d, 1H), 6.59 (s, 1H), 3.55 (s, 3H), 3.07 (s, 3H), 2.73 (s, 3H), 2.50-2.52 (m, 5H), 2.30-2.32 (m, 2H), 1.91-1.96 (m, 2H). Compound 2-307 (600 MHz, CDCl₃): 8.01 (d, 1H), 7.31 (d, 1H), 6.71 (s, 1H), 5.01 (s, 2H), 3.52 (s, 3H), 3.46 (s, 3H), 3.19 (s, 3H), 2.46 (s, 3H), 2.13-2.14 (m, 2H), 1.94-1.95 (m, 2H), 1.54-1.56 (m, 4H).

Compound 2-309 (600 MHz, CDCl₃): 8.03 (d, 1H), 7.33 (d, 1H), 6.60 (s, 1H), 5.03 (s, 2H), 3.56 (s, 3H), 3.48 (s, 3H), 3.22 (s, 3H), 2.49-2.52 (m, 5H), 2.30-2.33 (m, 2H), 1.91-1.96 (m, 2H).

Compound 2-343 (600 MHz, CDCl₃): 8.01 (d, 1H), 7.54 (q, 1H), 7.23 (d, 1H), 6.77-6.78 (m, 1H), 3.55 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.17 (q, 2H), 2.00-2.01 (m, 2H), 1.56-1.63 (m, 4H).

Compound 2-379 (600 MHz, DMSO-d₆): 8.22 (s, 1H), 8.16 (d, 1H), 7.61 (d, 1H), 6.58 (s, 1H), 3.51 (s, 3H), 3.32 (s, 3H), 2.36 (s, 3H), 2.02-2.04 (m, 2H), 1.85-1.87 (m, 2H), 1.40-1.50 (m, 4H).

Compound 2-380 (600 MHz, DMSO-d₆): 8.21 (s, 1H), 8.17 (d, 1H), 7.61 (d, 1H), 6.49 (s, 1H), 3.52 (s, 3H), 3.32 (s, 3H), 2.34-2.36 (m, 5H), 2.20-2.21 (m, 2H), 1.76-1.82 (m, 2H).

Compound 2-381 (600 MHz, CDCl₃): 8.05 (d, 1H), 7.34 (d, 1H), 6.74 (s, 1H), 5.16 (s, 2H), 3.77 (t, 2H), 3.56 (t, 2H), 3.55 (s, 3H), 3.34 (s, 3H), 3.29 (s, 3H), 2.50 (s, 3H), 2.16-2.17 (m, 2H), 1.98-1.99 (m, 2H), 1.57-1.61 (m, 4H).

Compound 2-382 (600 MHz, CDCl₃): 8.04 (d, 1H), 7.34 (d, 1H), 6.61 (s, 1H), 5.15 (s, 2H), 3.77 (t, 2H), 3.56-3.58 (m, 5H), 3.34 (s, 3H), 3.29 (s, 3H), 2.50-2.53 (m, 5H), 2.31-2.33 (m, 2H), 1.92-1.97 (m, 2H).

Compound 2-383 (600 MHz, CDCh3): 7.91 (s, 1H), 7.79 (d, 1H), 7.37 (d, 1H), 6.77 (s, 1H), 3.54 (s, 3H), 3.03 (s, 3H), 2.47 (s, 3H), 2.15-2.16 (m, 2H), 1.97-1.98 (m, 2H), 1.55-1.58 (m, 4H).

Compound 2-384 (600 MHz, CDCl₃): 7.93 (s, 1H), 7.81 (d, 1H), 7.40 (d, 1H), 6.67 (s, 1H), 3.58 (s, 3H), 3.07 (s, 3H), 2.49-2.52 (m, 5H), 2.33-2.34 (m, 2H), 1.93-1.96 (m, 2H).

Compound 2-385 (600 MHz, CDCl₃): 7.36 (s, 1H), 7.22 (d, 1H), 7.15 (d, 1H), 6.87 (s, 1H), 3.57 (s, 3H), 2.47 (s, 3H), 2.20-2.22 (m, 2H), 2.04-2.06 (m, 2H), 1.61-1.63 (m, 4H).

Compound 2-386 (600 MHz, CDCl₃): 7.36 (d, 1H), 7.24 (dd, 1H), 7.15 (d, 1H), 6.73 (s, 1H), 3.59 (s, 3H), 2.52-2.54 (m, 2H), 2.46 (s, 3H), 2.38-2.42 (m, 2H), 1.94-1.99 (m, 2H).

Compound 2-387 (600 MHz, CDCl₃): 8.66 (s, 1H), 8.19 (d, 1H), 7.55 (d, 1H), 6.75 (s, 1H), 3.52 (s, 3H), 3.11 (s, 3H), 2.52 (s, 3H), 2.18-2.21 (m, 2H), 1.92-1.93 (m, 2H), 1.57-1.64 (m, 4H).

Compound 2-388 (600 MHz, CDCl₃): 8.64 (s, 1H), 7.19 (d, 1H), 7.54 (d, 1H), 6.63 (s, 1H), 3.52 (s, 3H), 3.11 (s, 3H), 2.51-2.54 (m, 5H), 2.26-2.28 (m, 2H), 1.92-1.94 (m, 2H).

Compound 2-389 (600 MHz, CDCl₃): 8.21 (d, 1H), 8.10 (dd, 1H), 7.37 (d, 1H), 6.82 (t, 1H), 3.56 (s, 3H), 2.47 (s, 3H), 2.06-2.08 (m, 2H), 1.98-1.99 (m, 2H), 1.44-1.53 (m, 4H).

Compound 2-390 (600 MHz, CDCl₃): 8.20 (d, 1H), 8.09 (dd, 1H), 7.38 (d, 1H), 6.69 (s, 1H), 3.57 (s, 3H), 2.44 (s, 3H), 2.38-2.41 (m, 2H), 2.34-2.36 (m, 2H), 1.82-1.88 (m, 2H).

Compound 2-391 (600 MHz, CDCl₃): 8.09 (s, 1H), 7.63 (d, 1H), 7.28 (d, 1H), 6.83 (s, 1H), 3.52 (s, 3H), 2.51 (s, 3H), 2.20-2.21 (m, 2H), 1.98-1.99 (m, 2H), 1.62-1.64 (m, 4H).

Compound 2-392 (600 MHz, CDCl₃): 8.08 (s, 1H), 7.63 (d, 1H), 7.29 (d, 1H), 6.71 (s, 1H), 3.54 (s, 3H), 2.53-2.55 (m, 2H), 2.50 (s, 3H), 2.34-2.36 (m, 2H), 1.96-1.99 (m, 2H).

Compound 2-414 (600 MHz, CDCl₃): 7.83 (d, 1H), 7.07 (d, 1H), 6.90-6.91 (m, 1H), 4.77-4.81 (m, 1H), 3.57 (s, 3H), 3.19 (s, 3H), 2.36 (s, 3H), 2.23 (s, 3H), 2.17-2.20 (m, 2H), 2.05-2.07 (m, 2H), 1.57-1.63 (m, 4H), 1.34 (d, 6H).

Compound 2-415 (600 MHz, CDCl₃): 7.83 (d, 1H), 7.08 (d, 1H), 6.76-6.77 (m, 1H), 4.76-4.81 (m, 1H), 3.59 (s, 3H), 3.20 (s, 3H), 2.50-2.54 (m, 2H), 2.40-2.43 (m, 2H), 2.37 (s, 3H), 2.24 (s, 3H), 1.93-1.98 (m, 2H), 1.35 (d, 6H).

Compound 2-416 (600 MHz, CDCl₃): 7.79 (d, 1H), 7.11 (d, 1H), 6.76-6.78 (m, 1H), 4.16 (t, 2H), 3.79 (t, 2H), 3.55-3.59 (m, 4H), 3.47 (s, 3H), 3.24 (s, 3H), 2.24 (s, 3H), 2.17-2.19 (m, 2H), 1.96-1.97 (m, 2H), 1.59-1.63 (m, 4H), 1.32 (d, 6H).

Compound 2-417 (600 MHz, CDCl₃): 7.79 (d, 1H), 7.11 (d, 1H), 6.79-6.81 (m, 1H), 4.17 (t, 2H), 3.79 (t, 2H), 3.56 (s, 3H), 3.47 (s, 3H), 3.25 (s, 3H), 2.91 (q, 2H), 2.25 (s, 3H), 2.18-2.20 (m, 2H), 1.97-1.99 (m, 2H), 1.59-1.64 (m, 4H), 1.28 (t, 3H).

Compound 2-418 (600 MHz, CDCl₃): 7.81 (d, 1H), 7.16 (d, 1H), 7.09 (t, 1H), 6.86-6.87 (m, 1H), 4.17 (t, 2H), 3.79 (t, 2H), 3.69 (s, 3H), 3.47 (s, 3H), 3.26 (s, 3H), 2.27 (s, 3H), 2.18-2.20 (m, 2H), 1.98-2.00 (m, 2H), 1.59-1.63 (m, 4H).

Compound 2-419 (600 MHz, CDCl₃): 7.80 (d, 1H), 7.15 (d, 1H), 6.86-6.87 (m, 1H), 4.17 (t, 2H), 3.79 (t, 2H), 3.52 (s, 3H), 3.47 (s, 3H), 3.25 (s, 3H), 2.34-2.39 (m, 1H), 2.28 (s, 3H), 2.18-2.21 (m, 2H), 2.02-2.04 (m, 2H), 1.58-1.64 (m, 4H), 0.89-0.98 (m, 4H).

Compound 2-420 (600 MHz, CDCl₃): 7.80 (d, 1H), 7.12 (d, 1H), 6.85-6.87 (m, 1H), 4.17 (t, 2H), 3.85 (q, 2H), 3.79 (t, 2H), 3.47 (s, 3H), 3.25 (s, 3H), 2.44 (s, 3H), 2.26 (s, 3H), 2.19-2.21 (m, 2H), 2.02-2.04 (m, 2H), 1.57-1.62 (m, 4H), 1.38 (t, 3H).

Compound 2-421 (600 MHz, CDCl₃): 8.02 (d, 1H), 7.31 (d, 1H), 6.72-6.73 (m, 1H), 5.14 (s, 2H), 4.04-4.05 (m, 1H), 3.79-3.80 (m, 1H), 3.72-3.73 (m, 1H), 3.62-3.65 (m, 2H), 3.53 (s, 3H), 3.27 (s, 3H), 2.48 (s, 3H), 2.15-2.17 (m, 2H), 1.97-2.00 (m, 2H), 1.91-1.92 (m, 1H), 1.84-1.87 (m, 2H), 1.57-1.60 (m, 5H).

Compound 3-109 (600 MHz, CDCl₃): 8.64 (d, 1H), 7.88-7.92 (m, 1H), 7.63 (d, 1H), 7.51 (d, 2H), 7.39-7.47 (m, 3H), 7.33 (d, 1H), 6.22 (d, 1H), 3.67 (s, 3H), 2.40 (s, 3H).

Compound 4-140 (600 MHz, CDCl₃): 8.54 (d, 1H), 7.81-7.85 (m, 1H), 7.35 (d, 1H), 6.91-6.97 (m, 1H), 3.62 (s, 3H), 2.42 (s, 3H), 2.18-2.24 (m, 2H), 2.01-2.06 (m, 2H), 1.55-1.64 (m, 4H).

Compound 4-141 (600 MHz, CDCl₃): 8.56 (d, 1H), 7.83-7.87 (m, 1H), 7.35 (d, 1H), 6.80-6.85 (m, 1H), 3.62 (s, 3H), 2.50-2.55 (m, 2H), 2.38-2.43 (m, 5H), 1.89-2.00 (m, 2H).

Biometric Test Examples Embodiment 4 Determination of Herbicidal Activity

Seeds of broadleaf weeds (zinnia and piemarker) or grassy weeds (green bristlegrass and barnyard grass) were respectively sown in a paper cup having a diameter of 7 cm and containing nutrient soil; after sowing, the seeds were covered with 1 cm of soil, the soil was pressed and watered, and then the seeds were cultivated in a greenhouse according to a conventional method; and stems and leaves were sprayed after 2-3 leaf stage of the weeds.

After the original medicinal acetone was dissolved, the test requires to use 1‰ of Tween 80 to stand in running water to prepare the solution to be tested with a required concentration. According to the design dose of the test, spray treatment was carried out on a track-type crop sprayer (designed and produced by British Engineer Research Ltd.) (spray pressure is 1.95 kg/cm², spray volume is 500 L/hm² and track speed is 1.48 km/h). The test was repeated for three times. The test material was treated and then placed in an operation hall. The medicinal liquid was naturally dried in the shade, and then was placed in a greenhouse and managed according to the conventional method. The response of the weeds to the drug was observed and recorded. After treatment, the control effects of the test drug on the weeds were visually inspected regularly, expressed by 0-100%. “0” represents no control effect and “100%4” represents complete killing.

The test results show that the compounds of the formula I generally have high control effects on various weeds. Part of the test compounds, such as compounds 1-1, 1-7, 1-18, 1-20, 1-42, 1-76, 1-81, 1-82, 1-226, 1-259, 1-262, 1-265, 1-280, 1-292, 1-346, 1-349, 1-367, 1-370, 1-371, 2-1, 2-19, 2-37, 2-55, 2-67, 2-73, 2-121, 2-123, 2-289, 2-291, 2-307, 2-309, 2-379, 2-380, 2-383, 2-386, 2-391, 2416, 2417, 2-418, 2-419 and 2420, have good control effects on zinnia, piemarker, green bristlegrass or barnyard grass at the application dose of 600 g a.i./hm², and the control effects are greater than or equal to 90%.

According to the above test method, part of the compounds of the formula I and KC₁ are selected for activity test of controlling the zinnia. The results are shown in Table 5.

TABLE 5 Zinnia Control Activity of Part of Compounds of Formula 1 and Reference Compound KC₁ (after emergence, control effect %) dose g a.i./hm² Compound 600 150 37.5 1-42 100 100 100 1-81 100 95 90 KC₁ 0 0 0

According to the above test method, part of the compounds of the formula and KC₁ are selected for activity test of controlling the piemarker. The results are shown in Table 6.

TABLE 6 Piemarker Control Activity of Part of Compounds of Formula 1 and Reference Compound KC₁ (after emergence, control effect %) dose g a.i./hm² Compound 600 150 37.5 1-1 100 95 90 1-42 100 95 90 1-259 / 100 100 1 -292 95 90 90 KC₁ 100 70 20 “/” in the table indicates no test.

According to the above test method, part of the compounds of the formula I and KC₁ or KC₂ are selected for activity test of controlling the green bristlegrass. The results are shown in Table 7.

TABLE 7 Green Bristlegrass Control Activity of Part of Compounds of Formula 1 and Reference Compounds KC₁ or KC₂ (after emergence, control effect %) dose g a.i./hm² Compound 600 150 37.5 1-259 / 100 100 1-280 100 90 80 1 -292 95 90 90 KC₁ 10 10 10 2-121 98 90 80 2-123 100 100 90 KC₂ / 60 30 “/” in the table indicates no test.

According to the above test method, part of the compounds of the formula I and KC₁ or KC₂ are selected for activity test of controlling the barnyard grass. The results are shown in Table 8.

TABLE 8 Barnyard Grass Control Activity of Part of Compounds of Formula 1 and Reference Compounds KC₁ or KC₂ (after emergence, control effect %) dose g a.i./hm² Compound 600 150 37.5 1-42 100 95 80 1-81 95 90 80 1-82 100 95 90 1-259 / 100 100 1-280 100 95 85 1-292 100 95 90 KC₁ 0 0 0 2.37 100 100 95 2-67 100 100 90 2-73 100 100 95 2-123 100 100 100 KC₂ / 90 60 “/” in the table indicates no test.

To sum up, the alkene-containing carboxylic ester compound of the present invention has excellent herbicidal activity, also has high herbicidal activity at a lower dosage, and can be used for agriculturally controlling various weeds. 

1. An alkene-containing carboxylic ester compound, characterized in that the compound is shown in formula I:

in the formula: X₁ is selected from halogen, C₁-C₆ alkylsulfonyl, C₁-C₆ alkyl or C₁-C₆ haloalkyl; W is selected from CX₂; X₂ is selected from Y₁ oxy, Y₁ sulfonyl, Y₁ oxy C₁-C₆ alkyl, Y₁ sulfonyl C₁-C₆ alkyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkoxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl or halophenyl; Y₁ is selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkoxy, C₂-C₆ alkenyl, C₂-C₆ alkynyl, phenyl or halophenyl; X₃ is selected from halogen, C₁-C₆ alkylsulfonyl, C₁-C₆ alkyl or C₁-C₆ haloalkyl; when X₁ is selected from chlorine and X₃ is selected from methylsulfonyl, X₂ is not 2-thiazolyl; Z₁ is selected from C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkylsulfonyl C₁-C₆ alkyl or phenyl; Z₂ is selected from H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or C₁-C₆haloalkyl; Q is selected from Q₁ or Q₂ group;

Q₂ is selected from C₃-C₈ cycloalkenyl; the hydrogen on the ring can be substituted by the following substituents; the following substituents are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkenyl or C₃-C₆ cycloalkyl; when Q is selected from Q₂, Z₂ is not cyclopropyl; R₁ to R₅ are independently selected from hydrogen, cyano, nitro, halogen, phenyl, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio or benzyloxy; wherein R₁ and R₂ form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; R₂ and R₃ can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; a stereoisomer of the compound of the above formula I; or, the compound of the formula I and agriculturally acceptable salt of the isomer.
 2. The compound according to claim 1, characterized in that in the formula I: X₁ is selected from halogen, or C₁-C₆ alkyl; W is selected from CX₂; X₂ is selected from Y₁ oxy; Y₁ is selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy; X₃ is selected from C₁-C₆ alkylsulfonyl; Z₁ is selected from C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl or phenyl; Z₂ is selected from H, C₁-C₆ alkyl, C₁-C₆ haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or C₁-C₆ haloalkyl; Q is selected from Q₁ or Q₂ group;

Q₂ is selected from C₃-C₈ cycloalkenyl; the hydrogen on the ring can be substituted by the following substituents; the following substituents are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkenyl or C₃-C₆ cycloalkyl; R₁ to R₅ are independently selected from hydrogen, cyano, nitro, halogen, phenyl, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio or benzyloxy; wherein R₁ and R₂ form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; R₂ and R₃ can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; the Q of the above formula I is selected from a stereoisomer of the compound shown by Q₁.
 3. The compound according to claim 2, characterized in that in the formula I: X₁ is selected from halogen or C₁-C₃ alkyl; W is selected from CX₂; X₂ is selected from Y₁ oxy; Y₁ is selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy; X₃ is selected from C₁-C₃ alkylsulfonyl; Z₁ is selected from C₁-C₆ alkyl or C₃-C₆ cycloalkyl; Z₂ is selected from or C₁-C₆ alkyl; Q is selected from Q₁ or Q₂ group;

Q₂ is selected from cycloalkenyl; the hydrogen on the ring may be substituted by the following substituents which are selected from C₁-C₆ alkyl, C₁-C₆ alkoxy or C₁-C₆ alkenyl; R₁ to R₅ are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy or benzyloxy; the Q of the above formula I is selected from a stereoisomer of the compound shown by Q₁.
 4. The compound according to claim 3, characterized in that in the formula I: X₁ is selected from halogen or C₁-C₃ alkyl; W is selected from CX₂; X₂ is selected from Y₁ oxy; Y₁ is selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkyl C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C₁-C₆ alkyl containing 1-4 heteroatoms; the hydrogen on the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl or C₃-C₆ cycloalkoxy; X₃ is selected from C₁-C₃ alkylsulfonyl; Z₁ is selected from C₁-C₃ alkyl; Z₂ is selected from H or C₁-C₃ alkyl; Q is selected from Q₁ or Q₂ group;

Q₂ is selected from G1, G2, G3, G4, G5 or G6 group;

R₁ to R₅ are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, methyl, ethyl, propyl, vinyl, propenyl, ethynyl, propynyl, methoxy, ethoxyl, benzyloxy, trifluoromethyl or trifluoromethoxy; the Q of the above formula I is selected from a trans-stereoisomer of the compound shown by Q₁.
 5. An application of the compound of the formula I of claim 1, characterized in the application of the compound of the formula I and the stereoisomer thereof or the compound of the formula I and the agriculturally acceptable salt of the isomer in control for weeds.
 6. A herbicidal composition, characterized in that the herbicidal composition comprises an active ingredient and an agriculturally acceptable carrier; the active ingredient is a stereoisomer of the compound of the formula I of claim 1, or the compound of the formula I and agriculturally acceptable salt of the isomer; the weight percentage of the active ingredient in the composition is 1-99%.
 7. A method for controlling weeds by the composition of claim 6, characterized in that a herbicidally effective dose of the herbicidal composition of claim 6 is applied to a weed or a growth medium or site of the weed. 